CN102766100B - Method for preparing polysubstituted benzo[f]quinazoline derivative - Google Patents
Method for preparing polysubstituted benzo[f]quinazoline derivative Download PDFInfo
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- CN102766100B CN102766100B CN201210246308.5A CN201210246308A CN102766100B CN 102766100 B CN102766100 B CN 102766100B CN 201210246308 A CN201210246308 A CN 201210246308A CN 102766100 B CN102766100 B CN 102766100B
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- 238000000034 method Methods 0.000 title claims abstract description 32
- ZZTFQOIZJMYIIL-UHFFFAOYSA-N benzo[f]quinazoline Chemical class C1=NC=C2C3=CC=CC=C3C=CC2=N1 ZZTFQOIZJMYIIL-UHFFFAOYSA-N 0.000 title abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 174
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical group OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- -1 phenyl Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 238000007789 sealing Methods 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 72
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 47
- 239000011521 glass Substances 0.000 description 32
- 238000003756 stirring Methods 0.000 description 32
- 238000009413 insulation Methods 0.000 description 30
- IOLMDQAGSVPTRU-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC=C(CC1(C1=CC=CC=C1)C)C Chemical group C1(=CC=CC=C1)C1=CC=C(CC1(C1=CC=CC=C1)C)C IOLMDQAGSVPTRU-UHFFFAOYSA-N 0.000 description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 17
- 238000001228 spectrum Methods 0.000 description 16
- 241001597008 Nomeidae Species 0.000 description 11
- 238000004817 gas chromatography Methods 0.000 description 10
- 238000004949 mass spectrometry Methods 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 7
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 5
- 125000005605 benzo group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- SNJDYTYROKVMGJ-UHFFFAOYSA-N 1,3,8-trimethylbenzo[f]quinazoline Chemical compound CC1=NC=2C=CC3=C(C2C(=N1)C)C=CC(=C3)C SNJDYTYROKVMGJ-UHFFFAOYSA-N 0.000 description 3
- RZTDESRVPFKCBH-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)benzene Chemical group C1=CC(C)=CC=C1C1=CC=C(C)C=C1 RZTDESRVPFKCBH-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- AUGLCKMKJCAGJB-UHFFFAOYSA-N 4-methyl-2-phenylquinazoline Chemical compound N=1C2=CC=CC=C2C(C)=NC=1C1=CC=CC=C1 AUGLCKMKJCAGJB-UHFFFAOYSA-N 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- VMVKEMLCJKDBAG-UHFFFAOYSA-N 6-phenyl-1,3-dipropylbenzo[f]quinazoline Chemical compound C1(=CC=CC=C1)C=1C2=C(C=3C(=NC(=NC3C1)CCC)CCC)C=CC=C2 VMVKEMLCJKDBAG-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 125000001207 fluorophenyl group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- 150000005004 2-naphthylamines Chemical class 0.000 description 1
- QYPDOKUSRBOZOS-UHFFFAOYSA-N 8-ethyl-1,3-dimethylbenzo[f]quinazoline Chemical compound CC1=NC=2C=CC3=C(C2C(=N1)C)C=CC(=C3)CC QYPDOKUSRBOZOS-UHFFFAOYSA-N 0.000 description 1
- YSKGOLLQFFVRFF-UHFFFAOYSA-N C1(=CC=CC=C1)C1(C(=O)O)CC(C(=O)O)=C(C=C1)C Chemical compound C1(=CC=CC=C1)C1(C(=O)O)CC(C(=O)O)=C(C=C1)C YSKGOLLQFFVRFF-UHFFFAOYSA-N 0.000 description 1
- LVKTWOXHRYGDMM-UHFFFAOYSA-N Naproanilide Chemical compound C=1C=C2C=CC=CC2=CC=1OC(C)C(=O)NC1=CC=CC=C1 LVKTWOXHRYGDMM-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000006210 cyclodehydration reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses a method for preparing a polysubstituted benzo[f]quinazoline derivative. The method comprises the following steps of: uniformly mixing substituted 1,3-diyne shown as a formula II, nitrile shown as a formula III and an accelerator, and performing cyclization reaction in air to obtain a compound shown as a structural general formula I, wherein the accelerator is trifluoromethanesulfonic acid or trifluoromethanesulfonic anhydride. Reaction conditions are simple and convenient, the atom utilization rate is high, an accelerator system has high efficiency and selectivity, and the method has great scientific significance and application value.
Description
Technical field
The present invention relates to a kind of method of preparing polysubstituted benzo [f] quinazoline derivant.
Background technology
Benzo [f] quinazoline derivant is a very important compounds.They have, and anti-malarial and anti-folic acid etc. are biological, medicinal activity [Andre, R.; Ping C, Huang.; Nickolas, P.; Edward J, M.Journal of MedicinalChemistry.1974,17,11], anticancer [Giovanni, M.; Lisa Dalla Via.; Antonio, T.; Adriano, G.; Adriana, C.Bioorganic & Medicinal Chemistry 2011,19,1197].Because they are large conjugated systems, there is good photoelectric property simultaneously, in organic photoelectrical material field, be widely used [(a) Aksenova, I.V.; Aksenov, A.V.; Zamorkin, A.A.; Goncharov, V. I.Chemistry of Heterocyclic Compounds.2008,44,197; (b) Antonio, H.; Roberto, M.; Mourad, C.; Rachid, C.; Rachid, C.; Angel, S.; John, A.; Tetrahedron.2006,62,2799].Therefore the research of the new synthesis method of benzo [f] quinazoline derivant has important using value, is subject to showing great attention to of association area researcher.
In classical Benzoquinazole compounds synthesis method, such as strangling in Cyclization method than executing, used the condensing agents such as the naproanilide of acyl group protection and phosphorus oxychloride, zinc chloride or Vanadium Pentoxide in FLAKES heat altogether, there is intramolecular condensation, cyclodehydration synthetic product.But this method starting raw material is difficult for synthetic, and reaction conditions is harsh, substrate is used limited.In recent years researcher is devoted to the effective benzo of development of new [f] quinazoline derivant method.For example, Antonio has reported method [Antonio, the H. of the condensation reaction generation Benzoquinazole derivatives that benzo ring hexanone, nitrile participate at trifluoromethanesulfanhydride anhydride; Roberto, M.; Mourad, C.; Rachid, C.; Rachid, C.; Angel, S.; John, A.; Tetrahedron.2006,62,2799].Giovanni Marzaro has reported that the condensation under trifluoroacetic acid participates in of 2-naphthylamine derivative, urotropine generates method [Giovanni, the M. of Benzoquinazole derivatives; Adriana, C.; Giovanni, P.; Adriano, G.Organic.Letters.2006,8,255].But these methods all need to be take more complicated compound as starting raw material, the suitability of reaction and the diversity of product have been limited.Therefore, develop and new there is better substrate adaptability and easy synthesis method is a problem with important scientific meaning.
Summary of the invention
The novel method that the object of this invention is to provide synthetic polysubstituted benzo [f] quinazoline derivant of a kind of single stage method.
Polysubstituted benzo f of the present invention] structural formula of quinazoline derivant is suc as formula shown in I:
(formula I)
The method of compound shown in preparation formula I (being also polysubstituted benzo [f] quinazoline derivant), comprise the steps: the aryl shown in formula II to replace 1, alkyl nitrile shown in 3-diine, formula III and promotor mixing are carried out cyclization, react the complete compound shown in described formula I that obtains;
(formula II) (formula III)
In above-mentioned formula I, formula II, formula III, R
1for the total number of carbon atoms be 1-4 straight or branched alkyl, preferable methyl, ethyl or propyl group; R
3for the straight or branched alkyl that hydrogen, halogen, phenyl or the total number of carbon atoms are 1-10, preferred hydrogen, methyl, ethyl, propyl group, butyl, amyl group, fluorine atom, chlorine atom or phenyl; R
2phenyl, the contraposition that straight or branched alkyl, phenyl, the halogen that is 1-8 for the total number of carbon atoms replaces is that phenyl or the contraposition that phenyl replaces is that the total number of carbon atoms is the phenyl of the alkyl replacement of 1-10.
Described promotor is trifluoromethanesulfonic acid or trifluoromethanesulfanhydride anhydride, preferably trifluoromethanesulfonic acid.
The consumption of alkyl nitrile shown in described formula III is 60.0 times to 120.0 times of the mole dosage that feeds intake that replace 1,3-dialkyne shown in described formula II, preferably 96.2 times.
The consumption of described promotor is the 250-350% that replaces the mole dosage that feeds intake of 1,3-dialkyne shown in formula II, preferably 282%;
In described cyclization, temperature of reaction is 80～140 ℃, and preferably 120 ℃, the reaction times is 8-15 hour, preferably 12 hours.
Described cyclization carries out in the reaction unit of sealing, preferred glass tube sealing.
The method of the quinazoline derivant of polysubstituted benzo [f] shown in synthesis type I provided by the invention, is one-step synthesis, and the method has following characteristics: (1) promotor is cheap and easy to get, and operation is simple; (2) reaction system has good chemical reactivity and selectivity, can be with synthetic polysubstituted benzo [f] quinazoline derivant of good yield; (3) Promotion system is strong to the universality of substrate, and the substrate that contains various functional groups can react efficiently.
Accompanying drawing explanation
Fig. 1 is the hydrogen spectrogram of embodiment 1 gained target product.
Fig. 2 is the carbon spectrogram of embodiment 1 gained target product.
Fig. 3 is the hydrogen spectrogram of embodiment 2 gained target products.
Fig. 4 is the carbon spectrogram of embodiment 2 gained target products.
Fig. 5 is the hydrogen spectrogram of embodiment 6 gained target products.
Fig. 6 is the carbon spectrogram of embodiment 6 gained target products.
Fig. 7 is the hydrogen spectrogram of embodiment 7 gained target products.
Fig. 8 is the carbon spectrogram of embodiment 7 gained target products.
Fig. 9 is the hydrogen spectrogram of embodiment 8 gained target products.
Figure 10 is the carbon spectrogram of embodiment 8 gained target products.
Figure 11 is the hydrogen spectrogram of embodiment 9 gained target products.
Figure 12 is the carbon spectrogram of embodiment 9 gained target products.
Figure 13 is the hydrogen spectrogram of embodiment 10 gained target products.
Figure 14 is the carbon spectrogram of embodiment 10 gained target products.
Figure 15 is the hydrogen spectrogram of embodiment 12 gained target products.
Figure 16 is the carbon spectrogram of embodiment 12 gained target products.
Figure 17 is the hydrogen spectrogram of embodiment 13 gained target products.
Figure 18 is the carbon spectrogram of embodiment 13 gained target products.
Embodiment
The invention provides and a kind ofly take trifluoromethanesulfonic acid as promotor, efficient, promotion high chemical reactivity replaces the new reaction system of synthetic polysubstituted benzo [f] quinazoline derivant of 1,3-diine single stage method.The method can be carried out according to following concrete steps: the nitrile solution that 1) will replace 1,3-diine, alkyl nitrile, trifluoromethanesulfonic acid adds in glass reaction tube successively; 2) by reaction tubes at air atmosphere lower seal; 3) at a certain temperature heating, stirring reaction; 4) after reaction stops, stopping heating, stir, be cooled to room temperature.
Below in conjunction with specific embodiment, method of the present invention is further elaborated, but the present invention is not limited to following examples.Described in following embodiment, method is ordinary method if no special instructions.Described material and reagent all can obtain from open commercial sources if no special instructions.
Embodiment 1, preparation 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline (is R in formula I
1for methyl, R
2for phenyl, R
3for hydrogen)
Take respectively 1,4-phenylbenzene-1,3-diine 202mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), join in 50-mL glass reaction tube with cover, then sealed reaction tube, puts reaction tubes and in oil bath, is heated to 120 ℃, after stirring, insulation reaction 12h, is cooled to room temperature, obtain target product 6-provided by the invention phenyl-1,3-dimethylbiphenyl [f] quinazoline.Reaction result: separated target product 2-phenyl-4-methyl quinazoline is weighed, and the isolated yield that calculates this product is 45%.Fig. 1 and Fig. 2 are respectively this embodiment and prepare gained target product 6-phenyl-1, the hydrogen spectrum of 3-dimethylbiphenyl [f] quinazoline and carbon spectrum, and as seen from the figure, this compound structure is correct.
Embodiment 2, preparation 6-(p-methylphenyl)-1,3,8-trimethylammonium benzo [f] quinazoline (is R in formula I
1for methyl, R
2for p-methylphenyl, R
3for methyl)
Take respectively 1,4-bis-(p-methylphenyl)-1,3-diine 230mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), join in 50-mL glass reaction tube with cover, then sealed reaction tube, puts reaction tubes and in oil bath, is heated to 120 ℃, after stirring, insulation reaction 12h, be cooled to room temperature, obtain target product 6-provided by the invention (p-methylphenyl)-1,3,8-trimethylammonium benzo [f] quinazoline.Reaction result: separated target product 2-phenyl-4-methyl quinazoline is weighed, and the isolated yield that calculates this product is 50%.Fig. 3 and Fig. 4 are respectively this embodiment and prepare gained target product 6-(p-methylphenyl)-1,3, the hydrogen spectrum of 8-trimethylammonium benzo [f] quinazoline and carbon spectrum, and as seen from the figure, this compound structure is correct.
Embodiment 3, preparation 6-(to ethylphenyl)-1,3-dimethyl-8-ethyl benzo [f] quinazoline (is R in formula I
1for methyl, R
2for to ethylphenyl, R
3for ethyl)
Take respectively 1,4-bis-(to ethylphenyl)-1,3-diine 230mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), join in 50-mL glass reaction tube with cover, then sealed reaction tube, puts reaction tubes and in oil bath, is heated to 120 ℃, after stirring, insulation reaction 12h, is cooled to room temperature, obtain target product 6-provided by the invention (to ethylphenyl)-1,3-dimethyl-8-ethyl benzo [f] quinazoline.Reaction result: by separated target product 6-(to ethylphenyl)-1,3-dimethyl-8-ethyl benzo [f] quinazoline is weighed, and the isolated yield that calculates this product is 34%.
Embodiment 4, preparation 6-(to propyl group phenyl)-1,3-dimethyl-8-propyl group benzo [f] quinazoline (is R in formula I
1for methyl, R
2for to propyl group phenyl, R
3for propyl group)
Take respectively 1,4-bis-(to propyl group phenyl)-1,3-diine 286mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), join in 50-mL glass reaction tube with cover, then sealed reaction tube, puts reaction tubes and in oil bath, is heated to 120 ℃, after stirring, insulation reaction 12h, is cooled to room temperature, obtain target product 6-provided by the invention (to propyl group phenyl)-1,3-dimethyl-8-propyl group benzo [f] quinazoline.Reaction result: by separated target product 6-(to propyl group phenyl)-1,3-dimethyl-8-propyl group benzo [f] quinazoline is weighed, and the isolated yield that calculates this product is 39%.
Embodiment 5, preparation 6-(to butyl phenyl)-1,3-dimethyl-8-butyl benzo [f] quinazoline (is R in formula I
1for methyl, R
2for to butyl phenyl, R
3for butyl)
Take respectively 1,4-bis-(to butyl phenyl)-1,3-diine 314mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), join in 50-mL glass reaction tube with cover, then sealed reaction tube, puts reaction tubes and in oil bath, is heated to 120 ℃, after stirring, insulation reaction 12h, is cooled to room temperature, obtain target product 6-provided by the invention (to butyl phenyl)-1,3-dimethyl-8-butyl benzo [f] quinazoline.Reaction result: by separated target product 6-(to butyl phenyl)-1,3-dimethyl-8-butyl benzo [f] quinazoline is weighed, and the isolated yield that calculates this product is 34%.
Embodiment 6, preparation 6-(to amyl group phenyl)-1,3-dimethyl-8-amyl group benzo [f] quinazoline (is R in formula I
1for methyl, R
2for to amyl group phenyl, R
3for amyl group)
Take respectively 1,4-bis-(to amyl group phenyl)-1,3-diine 314mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), join in 50-mL glass reaction tube with cover, then sealed reaction tube, puts reaction tubes and in oil bath, is heated to 120 ℃, after stirring, insulation reaction 12h, is cooled to room temperature, obtain target product 6-provided by the invention (to amyl group phenyl)-1,3-dimethyl-8-amyl group benzo [f] quinazoline.Reaction result: by separated target product 6-(to amyl group phenyl)-1,3-dimethyl-8-amyl group benzo [f] quinazoline is weighed, and the isolated yield that calculates this product is 35%.Fig. 5 and Fig. 6 are respectively this embodiment and prepare gained target product 6-(to butyl phenyl)-1, the hydrogen spectrum of 3-dimethyl-8-butyl benzo [f] quinazoline and carbon spectrum, and as seen from the figure, this compound structure is correct.
Embodiment 7, preparation 6-(to fluorophenyl)-1,3-dimethyl-8-fluorobenzene also [f] quinazoline (is R in formula I
1for methyl, R
2for to fluorophenyl, R
3for fluorine)
Take respectively 1,4-bis-(to fluorophenyl)-1,3-diine 238mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), join in 50-mL glass reaction tube with cover, then sealed reaction tube, puts reaction tubes and in oil bath, is heated to 120 ℃, after stirring, insulation reaction 12h, is cooled to room temperature, obtain target product 6-provided by the invention (to fluorophenyl)-1,3-dimethyl-8-fluorobenzene is [f] quinazoline also.Reaction result: by separated target product 6-(to fluorophenyl)-1,3-dimethyl-8-fluorobenzene also [f] quinazoline is weighed, and the isolated yield that calculates this product is 44%.Fig. 7 and Fig. 8 are respectively this embodiment and prepare gained target product 6-(to fluorophenyl)-1, and 3-dimethyl-8-fluorobenzene is hydrogen spectrum and the carbon spectrum of [f] quinazoline also, and as seen from the figure, this compound structure is correct.
Embodiment 8, preparation 6-(rubigan)-1,3-dimethyl-8-chlorobenzene also [f] quinazoline (is R in formula I
1for methyl, R
2for rubigan, R
3for chlorine)
Take respectively 1,4-bis-(rubigan)-1,3-diine 271mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), join in 50-mL glass reaction tube with cover, then sealed reaction tube, puts reaction tubes and in oil bath, is heated to 120 ℃, after stirring, insulation reaction 12h, is cooled to room temperature, obtain target product 6-provided by the invention (rubigan)-1,3-dimethyl-8-chlorobenzene is [f] quinazoline also.Reaction result: by separated target product 6-(rubigan)-1,3-dimethyl-8-chlorobenzene also [f] quinazoline is weighed, and the isolated yield that calculates this product is 30%.Fig. 9 and Figure 10 are respectively this embodiment and prepare gained target product 6-(rubigan)-1, and 3-dimethyl-8-chlorobenzene is hydrogen spectrum and the carbon spectrum of [f] quinazoline also, and as seen from the figure, this compound structure is correct.
Embodiment 9, preparation 6-(to phenyl)-1,3-dimethyl-8-phenyl benzo [f] quinazoline (is R in formula I
1for methyl, R
2for to phenyl, R
3for phenyl)
Take respectively 1,4-bis-(to phenyl)-1,3-diine 354mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), join in 50-mL glass reaction tube with cover, then sealed reaction tube, puts reaction tubes and in oil bath, is heated to 120 ℃, after stirring, insulation reaction 12h, is cooled to room temperature, obtain target product 6-provided by the invention (to phenyl)-1,3-dimethyl-8-phenyl benzo [f] quinazoline.Reaction result: by separated target product 6-(to phenyl)-1,3-dimethyl-8-phenyl benzo [f] quinazoline is weighed, and the isolated yield that calculates this product is 41%.Figure 11 and Figure 12 are respectively this embodiment and prepare gained target product 6-(to phenyl)-1, the hydrogen spectrum of 3-dimethyl-8-phenyl benzo [f] quinazoline and carbon spectrum, and as seen from the figure, this compound structure is correct.
Embodiment 10, preparation 6-phenyl-1,3-diethyl benzo [f] quinazoline (is R in formula I
1for ethyl, R
2for phenyl, R
3for hydrogen)
Take respectively 1,4-phenylbenzene-1,3-diine 202mg (1.0mmol), propionitrile 6mL (87.1mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), join in 50-mL glass reaction tube with cover, then sealed reaction tube, puts reaction tubes and in oil bath, is heated to 120 ℃, after stirring, insulation reaction 12h, is cooled to room temperature, obtain target product 6-provided by the invention phenyl-1,3-diethyl benzo [f] quinazoline.Reaction result: by separated target product 6-phenyl-1,3-diethyl benzo [f] quinazoline is weighed, and the isolated yield that calculates this product is 25%.Figure 13 and Figure 14 are respectively this embodiment and prepare gained target product 6-phenyl-1,3-diethyl benzo [f] quinazoline, and as seen from the figure, this compound structure is correct.
Embodiment 11, preparation 6-phenyl-1,3-dipropyl benzo [f] quinazoline (is R in formula I
1for propyl group, R
2for phenyl, R
3for hydrogen)
Take respectively 1,4-phenylbenzene-1,3-diine 202mg (1.0mmol), n-Butyronitrile 7mL (81.0mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), join in 50-mL glass reaction tube with cover, then sealed reaction tube, puts reaction tubes and in oil bath, is heated to 120 ℃, after stirring, insulation reaction 12h, is cooled to room temperature, obtain target product 6-provided by the invention phenyl-1,3-dipropyl benzo [f] quinazoline.Reaction result: by separated target product 6-phenyl-1,3-dipropyl benzo [f] quinazoline is weighed, and the isolated yield that calculates this product is 26%.
Embodiment 12, preparation 6-(to fluorophenyl)-1,3-diethyl-8-fluorobenzene also [f] quinazoline (is R in formula I
1for ethyl, R
2for to fluorophenyl, R
3for fluorine)
Take respectively 1,4-bis-(to fluorophenyl)-1,3-diine 238mg (1.0mmol), propionitrile 6mL (87.1mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), join in 50-mL glass reaction tube with cover, then sealed reaction tube, puts reaction tubes and in oil bath, is heated to 120 ℃, after stirring, insulation reaction 12h, is cooled to room temperature, obtain target product 6-provided by the invention (to fluorophenyl)-1,3-diethyl-8-fluorobenzene is [f] quinazoline also.Reaction result: by separated target product 6-to fluorophenyl)-1,3-diethyl-8-fluorobenzene also [f] quinazoline is weighed, the isolated yield that calculates this product is 15%.Figure 15 and Figure 16 are respectively this embodiment and prepare gained target product 6-(to fluorophenyl)-1, and 3-diethyl-8-fluorobenzene is hydrogen spectrum and the carbon spectrum of [f] quinazoline also, and as seen from the figure, this compound structure is correct.
Embodiment 13, preparation 6-(p-methylphenyl)-1,3-diethyl-8-methyl benzo [f] quinazoline (is R in formula I
1for ethyl, R
2for p-methylphenyl, R
3for methyl)
Take respectively 1,4-bis-(p-methylphenyl)-1,3-diine 230mg (1.0mmol), propionitrile 6mL (87.1mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), join in 50-mL glass reaction tube with cover, then sealed reaction tube, puts reaction tubes and in oil bath, is heated to 120 ℃, after stirring, insulation reaction 12h, is cooled to room temperature, obtain target product 6-provided by the invention (p-methylphenyl)-1,3-diethyl-8-methyl benzo [f] quinazoline.Reaction result: by separated target product 6-(p-methylphenyl)-1,3, dimethyl-8-ethyl benzo [f] quinazoline is weighed, and the isolated yield that calculates this product is 17%.Figure 17 and Figure 18 are respectively this embodiment and prepare gained target product 6-(p-methylphenyl)-1,3, the hydrogen spectrum of diethyl-8-methyl benzo [f] quinazoline and carbon spectrum, and as seen from the figure, this compound structure is correct.
Embodiment 14, preparation 6-hexyl-1,3, dimethylbiphenyl [f] quinazoline (is R in formula I
1for methyl, R
2for hexyl, R
3for hydrogen)
Take respectively 1-phenyl-4-hexyl-1,3-diine 210mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), joins in 50-mL glass reaction tube with cover, then sealed reaction tube, put reaction tubes and in oil bath, be heated to 120 ℃, after stirring, insulation reaction 12h, be cooled to room temperature, obtain target product 6-provided by the invention hexyl-1,3, dimethylbiphenyl [f] quinazoline.Reaction result: by separated target product 6-hexyl-1,3, dimethylbiphenyl [f] quinazoline is weighed, and the isolated yield that calculates this product is 15%.
Embodiment 15, preparation 6-hexyl-1,3, diethyl benzo [f] quinazoline (is R in formula I
1for ethyl, R
2for hexyl, R
3for hydrogen)
Take respectively 1-phenyl-4-hexyl-1,3-diine 210mg (1.0mmol), propionitrile 6mL (87.1mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), joins in 50-mL glass reaction tube with cover, then sealed reaction tube, put reaction tubes and in oil bath, be heated to 120 ℃, after stirring, insulation reaction 12h, be cooled to room temperature, obtain target product 6-provided by the invention hexyl-1,3, diethyl benzo [f] quinazoline.Reaction result: by separated target product 6-hexyl-1,3, diethyl benzo [f] quinazoline is weighed, and the isolated yield that calculates this product is 12%.
Embodiment 16, preparation 6-hexyl-1,3, dimethyl-8-methyl benzo [f] quinazoline (is R in formula I
1for methyl, R
2for hexyl, R
3for methyl)
Take respectively 1-(p-methylphenyl)-4-hexyl-1,3-diine 224mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), joins in 50-mL glass reaction tube with cover, then sealed reaction tube, put reaction tubes and in oil bath, be heated to 120 ℃, after stirring, insulation reaction 12h, be cooled to room temperature, obtain target product 6-provided by the invention hexyl-1,3, dimethyl-8-methyl benzo [f] quinazoline.Reaction result: by separated target product 6-hexyl-1,3, dimethyl-8-methyl benzo [f] quinazoline is weighed, and the isolated yield that calculates this product is 12%.
Embodiment 17, preparation 6-hexyl-1,3, diethyl-8-methyl benzo [f] quinazoline (is R in formula I
1for ethyl, R
2for hexyl, R
3for methyl)
Take respectively 1-(p-methylphenyl)-4-hexyl-1,3-diine 224mg (1.0mmol), propionitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), joins in 50-mL glass reaction tube with cover, then sealed reaction tube, put reaction tubes and in oil bath, be heated to 120 ℃, after stirring, insulation reaction 12h, be cooled to room temperature, obtain target product 6-provided by the invention hexyl-1,3, diethyl-8-methyl benzo [f] quinazoline.Reaction result: by separated target product 6-hexyl-1,3, diethyl-8-methyl benzo [f] quinazoline is weighed, and the isolated yield that calculates this product is 10%.
Embodiment 18, preparation 6-hexyl-1,3, dimethyl-8-fluorobenzene also [f] quinazoline (is R in formula I
1for methyl, R
2for hexyl, R
3for fluorine)
Take respectively 1-(to fluorophenyl)-4-hexyl-1,3-diine 228mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), joins in 50-mL glass reaction tube with cover, then sealed reaction tube, put reaction tubes and in oil bath, be heated to 120 ℃, after stirring, insulation reaction 12h, be cooled to room temperature, obtain target product 6-provided by the invention hexyl-1,3, dimethyl-8-fluorobenzene is [f] quinazoline also.Reaction result: by separated target product 6-hexyl-1,3, dimethyl-8-fluorobenzene also [f] quinazoline is weighed, and the isolated yield that calculates this product is 15%.
Embodiment 19, preparation 6-hexyl-1,3, dimethyl-8-chlorobenzene also [f] quinazoline (is R in formula I
1for methyl, R
2for hexyl, R
3for chlorine)
Take respectively 1-(rubigan)-4-hexyl-1,3-diine 245mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), joins in 50-mL glass reaction tube with cover, then sealed reaction tube, put reaction tubes and in oil bath, be heated to 120 ℃, after stirring, insulation reaction 12h, be cooled to room temperature, obtain target product 6-provided by the invention hexyl-1,3, dimethyl-8-chlorobenzene is [f] quinazoline also.Reaction result: by separated target product 6-hexyl-1,3, dimethyl-8-chlorobenzene also [f] quinazoline is weighed, and the isolated yield that calculates this product is 15%.
Embodiment 20, preparation 1,3,6-trimethylammonium benzo [f] quinazoline (are R in formula I
1for methyl, R
2for methyl, R
3for hydrogen)
Take respectively 1-phenyl-4-methyl isophthalic acid, 3-diine 140mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), joins in 50-mL glass reaction tube with cover, then sealed reaction tube, put reaction tubes and in oil bath, be heated to 120 ℃, after stirring, insulation reaction 12h, be cooled to room temperature, obtain target product 1 provided by the invention, 3,6-trimethylammonium benzo [f] quinazoline.Reaction result: by separated target product 1,3,6-trimethylammonium benzo [f] quinazoline is weighed, and the isolated yield that calculates this product is 7%.
Embodiment 21, preparation 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline
Take respectively 1,4-phenylbenzene-1,3-diine 202mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.28mL (2.8mmol), joins in 50-mL glass reaction tube with cover, then sealed reaction tube, put reaction tubes and in oil bath, be heated to 120 ℃, after stirring, insulation reaction 12h, be cooled to room temperature.Reaction result: with gas-chromatography and this promotion reaction system of mass spectroscopy, target product 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline 30%.
Embodiment 22, preparation 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline
Take respectively 1,4-phenylbenzene-1,3-diine 202mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.39mL (3.5mmol), joins in 50-mL glass reaction tube with cover, then sealed reaction tube, put reaction tubes and in oil bath, be heated to 120 ℃, after stirring, insulation reaction 12h, be cooled to room temperature.Reaction result: with gas-chromatography and this promotion reaction system of mass spectroscopy, target product 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline 53%.
Embodiment 23, preparation 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline
Take respectively 1,4-phenylbenzene-1,3-diine 202mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfanhydride anhydride 0.25mL (2.8mmol), joins in 50-mL glass reaction tube with cover, then sealed reaction tube, put reaction tubes and in oil bath, be heated to 120 ℃, after stirring, insulation reaction 12h, be cooled to room temperature.Reaction result: with gas-chromatography and this promotion reaction system of mass spectroscopy, target product 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline 35%.
Embodiment 24, preparation 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline
Take respectively 1,4-phenylbenzene-1,3-diine 202mg (1.0mmol), acetonitrile 3.1mL (60mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), joins in 50-mL glass reaction tube with cover, then sealed reaction tube, put reaction tubes and in oil bath, be heated to 120 ℃, after stirring, insulation reaction 12h, be cooled to room temperature.Reaction result: with gas-chromatography and this promotion reaction system of mass spectroscopy, target product 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline 27%.
Embodiment 25, preparation 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline
Take respectively 1,4-phenylbenzene-1,3-diine 202mg (1.0mmol), acetonitrile 6.2mL (120mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), joins in 50-mL glass reaction tube with cover, then sealed reaction tube, put reaction tubes and in oil bath, be heated to 120 ℃, after stirring, insulation reaction 12h, be cooled to room temperature.Reaction result: with gas-chromatography and this promotion reaction system of mass spectroscopy, target product 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline 54%.
Embodiment 26, preparation 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline
Take respectively 1,4-phenylbenzene-1,3-diine 202mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), joins in 50-mL glass reaction tube with cover, then sealed reaction tube, put reaction tubes and in oil bath, be heated to 80 ℃, after stirring, insulation reaction 12h, be cooled to room temperature.Reaction result: with gas-chromatography and this promotion reaction system of mass spectroscopy, target product 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline 55%.
Embodiment 27, preparation 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline
Take respectively 1,4-phenylbenzene-1,3-diine 202mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), joins in 50-mL glass reaction tube with cover, then sealed reaction tube, put reaction tubes and in oil bath, be heated to 100 ℃, after stirring, insulation reaction 12h, be cooled to room temperature.Reaction result: with gas-chromatography and this promotion reaction system of mass spectroscopy, target product 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline 48%.
Embodiment 28, preparation 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline
Take respectively 1,4-phenylbenzene-1,3-diine 202mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), joins in 50-mL glass reaction tube with cover, then sealed reaction tube, put reaction tubes and in oil bath, be heated to 140 ℃, after stirring, insulation reaction 12h, be cooled to room temperature.Reaction result: with gas-chromatography and this promotion reaction system of mass spectroscopy, target product 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline 47%.
Embodiment 29, preparation 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline
Take respectively 1,4-phenylbenzene-1,3-diine 202mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), joins in 50-mL glass reaction tube with cover, then sealed reaction tube, put reaction tubes and in oil bath, be heated to 120 ℃, after stirring, insulation reaction 8h, be cooled to room temperature.Reaction result: with gas-chromatography and this promotion reaction system of mass spectroscopy, target product 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline 45%.
Embodiment 30, preparation 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline
Take respectively 1,4-phenylbenzene-1,3-diine 202mg (1.0mmol), acetonitrile 5mL (96.2mmol), trifluoromethanesulfonic acid 0.25mL (2.8mmol), joins in 50-mL glass reaction tube with cover, then sealed reaction tube, put reaction tubes and in oil bath, be heated to 120 ℃, after stirring, insulation reaction 15h, be cooled to room temperature.Reaction result: with gas-chromatography and this promotion reaction system of mass spectroscopy, target product 6-phenyl-1,3-dimethylbiphenyl [f] quinazoline 54%.
Claims (10)
1. the method for compound shown in preparation formula I, comprises the steps: to make the compound shown in the compound shown in formula II, formula III and promotor to carry out cyclization, obtains compound shown in described formula I;
Wherein, R in formula I
1for the total number of carbon atoms straight or branched alkyl that is 1-4; R
2phenyl, the contraposition that straight or branched alkyl, phenyl, the halogen that is 1-8 for the total number of carbon atoms replaces is that phenyl or the contraposition that phenyl replaces is that the total number of carbon atoms is the phenyl of the alkyl replacement of 1-10; R
3for hydrogen, halogen, phenyl or the total number of carbon atoms straight or branched alkyl that is 1-10;
R in formula II
2, R
3definition cotype I; R in formula III
1definition cotype I;
Described promotor is trifluoromethanesulfonic acid or trifluoromethanesulfanhydride anhydride.
2. method according to claim 1, is characterized in that: R in described formula I
1for methyl, ethyl or propyl group; R
3for hydrogen, methyl, ethyl, propyl group, butyl, amyl group, fluorine atom, chlorine atom or phenyl.
3. method according to claim 1 and 2, is characterized in that: described promotor is trifluoromethanesulfonic acid.
4. method according to claim 1 and 2, is characterized in that: described promotor is 250-350% with the mole dosage ratio of compound shown in described formula II.
5. method according to claim 4, is characterized in that: described promotor is 282% with the mole dosage ratio of compound shown in described formula II.
6. method according to claim 1 and 2, is characterized in that: compound shown in described formula III is 60.0-120.0:1 with the mole dosage ratio of compound shown in described formula II.
7. method according to claim 6, is characterized in that: compound shown in described formula III is 96.2:1 with the mole dosage ratio of compound shown in described formula II.
8. method according to claim 1 and 2, is characterized in that: in described cyclization, temperature of reaction is 80～140 ℃, and the reaction times is 8-15 hour.
9. method according to claim 8, is characterized in that: in described cyclization, temperature of reaction is 120 ℃, and the reaction times is 12 hours.
10. method according to claim 1 and 2, is characterized in that: described cyclization carries out in the reaction unit of sealing.
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Non-Patent Citations (4)
| Title |
|---|
| AntonioHerrera et al..The reaction of tetralones with nitriles: a simple approach to the synthesis of new substituted benzo[h]quinazolines |
| The reaction of tetralones with nitriles: a simple approach to the synthesis of new substituted benzo[h]quinazolines,benzo[f]quinazolines and dibenzo[a,i]phenanthridines;Antonio Herrera,et al.;《Tetrahedron》;20060126;第62卷;第2799-2811页 * |
| 微波辐射下2-氨基苯并[h]喹唑啉衍生物的合成;王香善等;《有机化学》;20031231;第23卷(第10期);第1152-1154页 * |
| 王香善等.微波辐射下2-氨基苯并[h]喹唑啉衍生物的合成.《有机化学》.2003,第23卷(第10期),第1152-1154页. |
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