CN109369672B - Preparation method of polysubstituted cycloheptatriene derivative - Google Patents
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- CHVJITGCYZJHLR-UHFFFAOYSA-N cyclohepta-1,3,5-triene Chemical class C1C=CC=CC=C1 CHVJITGCYZJHLR-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000012043 crude product Substances 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 7
- ZBIKORITPGTTGI-UHFFFAOYSA-N [acetyloxy(phenyl)-$l^{3}-iodanyl] acetate Chemical compound CC(=O)OI(OC(C)=O)C1=CC=CC=C1 ZBIKORITPGTTGI-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000047 product Substances 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 4
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical group OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 238000001311 chemical methods and process Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- -1 methoxy, methyl Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000000706 filtrate Substances 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 40
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 8
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- QAFBDGXIYRHBDO-UHFFFAOYSA-N 2-diazoethyl acetate Chemical compound CC(=O)OCC=[N+]=[N-] QAFBDGXIYRHBDO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- REDUQXCPUSNJOL-UHFFFAOYSA-N C(C1=CC=CC=C1)NC(CN(C(C1=CC=C(C=C1)C(C)C)=O)CC1=CC=C(C=C1)C(NO)=O)=O Chemical compound C(C1=CC=CC=C1)NC(CN(C(C1=CC=C(C=C1)C(C)C)=O)CC1=CC=C(C=C1)C(NO)=O)=O REDUQXCPUSNJOL-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 1
- SRVFFFJZQVENJC-IHRRRGAJSA-N aloxistatin Chemical compound CCOC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C SRVFFFJZQVENJC-IHRRRGAJSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- YMNCVRSYJBNGLD-KURKYZTESA-N cephalotaxine Chemical compound C([C@@]12C=C([C@H]([C@H]2C2=C3)O)OC)CCN1CCC2=CC1=C3OCO1 YMNCVRSYJBNGLD-KURKYZTESA-N 0.000 description 1
- DSRNKUZOWRFQFO-UHFFFAOYSA-N cephalotaxine Natural products COC1=CC23CCCN2CCc4cc5OCOc5cc4C3=C1O DSRNKUZOWRFQFO-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000006049 ring expansion reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of polysubstituted cycloheptatriene derivatives, belonging to the technical field of organic synthesis. The method comprises the following steps: to the reactor, substituted N-alkylbenzamide, iodobenzene diacetate were added. After the reaction in the solvent is completed by stirring, the filtrate is concentrated by using a rotary evaporator to obtain a crude product, and the crude product is separated by silica gel column chromatography to obtain the target compound. The synthesis method of the polysubstituted cycloheptatriene derivative provided by the invention has the characteristics of scientificity, reasonableness, simplicity, high yield of target compounds, easiness in product purification, rapidness in reaction, room temperature reaction and the like. The reaction equation is as follows:
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of a cycloheptatriene derivative.
Background
The cycloheptatriene derivatives are widely present in nature, and many drugs or drug intermediates contain a cycloheptatriene derivative structural unit. Most of the cycloheptatriene derivatives have biological activities of resisting tumor, bacteria, viruses, inflammation, ulcer, insects and the like, since the 90 s of the 20 th century, the research on drugs based on the cycloheptatriene derivatives and modified products of the structures thereof is vigorous, the structural types of the cycloheptatriene derivatives are continuously increased, the anti-tumor effect is a hot field of the research, and various structures show better anti-tumor activity. The structure of the cycloheptatriene derivative is widely existed in a plurality of medicines, such as penicillin spiral derivative, cephalotaxine, KT1-32 and the like. ((a) J.Am.chem.Soc.1998,120,8,1914-1915(b) J.org.chem.2004,69,25,8652-8667(c) org.Lett.2001,3,7,1081-1084)
In view of the wide biological activity and application value of the cycloheptatriene derivatives, it is of great significance to develop a new method for synthesizing the cycloheptatriene derivatives practically and efficiently.
The method for synthesizing the cycloheptatriene derivative comprises the following steps:
in 1885, E.Buchner and T.Curtius reacted carbene, generated by thermal and photochemical routes with diazoethylacetate, with benzene to produce a cycloheptatriene derivative. Later, a mode that the transition metal catalyzes the generation of metal carbene and then generates ring expansion reaction to generate the cycloheptatriene derivative is developed. (a) J.Am.chem.Soc.2012,134,7588-7591 (b) J.Am.chem.Soc.1996,118, 8162-3.) the reaction scheme is shown in formula I:
the above-described process for preparing polysubstituted cycloheptatriene derivatives has significant disadvantages: the reaction time is long, noble metals are used in the reaction, and the danger of reaction substrates is high.
Disclosure of Invention
In order to overcome the disadvantages of the prior art, the method is used as a supplement to the prior method for synthesizing the cycloheptatriene derivative. The invention provides a method for rapidly preparing polysubstituted cycloheptatriene derivatives at room temperature under the promotion of iodine (III).
A method for preparing a polysubstituted cycloheptatriene derivative, wherein the cycloheptatriene derivative has a structure shown as a formula II:
R1the substituent group is selected from fluorine, chlorine, bromine, methoxy and methyl; r2The substituent group is selected from methoxy, methyl, fluorine, chlorine and bromine; the method is characterized in that N-alkoxy benzamide substances connected with alkynyl and iodobenzene diacetate are added into a reactor. After the stirring reaction in the solvent is finished, concentrating by using a rotary evaporator to obtain a crude product, and separating the crude product by using silica gel column chromatography to obtain a target product, wherein the chemical process is shown as a reaction formula III:
the molar ratio of the substituted N-alkoxy benzamide to the iodobenzene diacetate is 1: 1.2. the solvent is trifluoroethanol, the reaction temperature is room temperature, and the reaction time is 1 min.
The invention has the beneficial effects that: the synthesis method of the polysubstituted cycloheptatriene derivative provided by the invention is scientific and reasonable, provides a new way for synthesizing the polysubstituted cycloheptatriene derivative, obtains the cycloheptatriene derivative with various substituent groups by the method, and is characterized in that: the synthesis method is simple, the yield of the target compound is high, the product is easy to purify, the reaction is rapid, and the reaction condition is room temperature.
Drawings
FIG. 1 is an NMR spectrum of Compound 2a prepared in example 1;
FIG. 2 is an NMR spectrum of Compound 2b prepared in example 2;
FIG. 3 is an NMR spectrum of compound 2h prepared in example 8.
Detailed Description
The invention is described in further detail below with reference to the following figures and specific examples:
the test methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
Example 1
1) Preparation of cycloheptatriene derivatives 2a
To a 25mL round-bottomed flask were added N-alkoxybenzamide 1a (0.2mmol,55.9mg) and iodobenzene diacetate (0.24mmol, 77.3mg), and trifluoroethanol (4mL) was added, followed by stirring at room temperature to conduct a reaction for 1 minute. After the reaction is finished, the solvent is removed by using a rotary evaporator to obtain a crude product, the crude product is separated by column chromatography (200-mesh silica gel 300) (petroleum ether/ethyl acetate: 4/1), and the solvent is removed by using the rotary evaporator to obtain the target product, namely the unsubstituted cycloheptatriene derivative 2a, wherein the yield is 87%.
1H NMR(500MHz,CDCl3)δ7.26(d,J＝3.1Hz,1H),7.16(s,5H),6.50–6.42(m,3H),6.12–6.06(m,1H),5.06(t,J＝4.3Hz,1H),4.25(qt,J＝10.9,5.2Hz,2H),2.46–2.26(m,2H).13C NMR(125MHz,CDCl3)δ157.56,142.91,141.03,133.64,129.08,128.64,128.03,127.73,127.43,127.13,125.79,125.35,95.07,69.25,49.79,22.59.
example 2
1a in example 1 is replaced by 1b, other conditions are the same as example 1, and the experimental results are shown in Table 1.
1H NMR(500MHz,CDCl3)δ7.13(d,J＝13.5Hz,6H),6.28(d,J＝10.2Hz,1H),6.23(d,J＝6.1Hz,1H),6.01(d,J＝10.2Hz,1H),4.99(t,J＝4.2Hz,1H),4.23(qt,J＝10.9,5.3Hz,2H),2.43–2.25(m,2H),1.88(s,3H).13C NMR(125MHz,CDCl3)δ157.96,143.73,143.08,141.49,130.80,128.05,127.74,127.01,126.29,125.79,125.61,125.34,94.76,69.24,49.38,24.68,22.59.
example 3
1a in example 1 is replaced by 1c, other conditions are the same as in example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 2c:
1H NMR(500MHz,CDCl3)δ7.16(d,J＝25.1Hz,6H),6.61(d,J＝5.9Hz,1H),6.46(d,J＝10.0Hz,1H),6.08(d,J＝10.1Hz,1H),5.04(s,1H),4.25(s,2H),2.47–2.23(m,2H).13C NMR(125MHz,CDCl3)δ157.13,142.40,140.36,138.44,130.05,129.44,128.74,128.16,127.61,127.43,125.58,123.51,95.72,69.37,49.57,22.57.
example 4
1a in example 1 is replaced by 1d, other conditions are the same as in example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 2d:
1H NMR(500MHz,CDCl3)δ7.21(s,5H),6.57–6.40(m,2H),6.31(t,J＝10.9Hz,2H),5.01(s,1H),4.31–4.15(m,2H),2.46–2.23(m,2H).13C NMR(125MHz,CDCl3)δ159.86,157.76,155.74,142.29,141.04,135.42,135.31,133.04,127.91,127.42,126.41,125.74,123.11,122.85,94.88,69.18,22.57.
example 5
1a in example 1 is replaced by 1e, other conditions are the same as in example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 2e:
1H NMR(500MHz,CDCl3)δ7.26(t,J＝2.7Hz,1H),7.15–7.11(m,2H),7.09(t,J＝8.0Hz,1H),7.03(d,J＝7.6Hz,1H),6.48(dd,J＝8.8,3.1Hz,3H),6.05(dd,J＝8.5,2.3Hz,1H),5.06(t,J＝4.3Hz,1H),4.25(qt,J＝11.0,5.1Hz,2H),2.47–2.26(m,2H).13C NMR(125MHz,CDCl3)δ157.30,143.11,142.27,129.03,128.80,128.38,127.84,127.54,127.40,126.01,125.61,95.54,69.25,49.49,22.57.
example 6
1f is used instead of 1a in example 1, the conditions are the same as in example 1, and the experimental results are shown in Table 1.
Spectrum analysis data 2f:
1H NMR(500MHz,CDCl3)δ7.23(t,J＝8.1Hz,2H),7.11(t,J＝6.7Hz,2H),7.05(t,J＝7.3Hz,1H),6.54–6.42(m,3H),5.80(d,J＝9.1Hz,1H),5.08(s,1H),4.29(dh,J＝17.3,6.4,5.7Hz,2H),2.49–2.27(m,2H).13C NMR(125MHz,CDCl3)δ158.03,141.11,134.99,133.61,132.40,131.49,129.62,128.48,128.37,126.97,125.35,123.31,122.36,95.76,68.90,48.32,22.68.
example 7
1a in example 1 was replaced by 1g, and the experimental results are shown in Table 1, except that the conditions were the same as in example 1.
Spectrogram analysis data 2g:
1H NMR(500MHz,CDCl3)δ7.48–7.41(m,2H),7.30–7.23(m,3H),6.54–6.42(m,3H),6.07(d,J＝9.5Hz,1H),5.04(t,J＝4.2Hz,1H),4.24(ddq,J＝21.5,10.9,5.1,4.6Hz,2H),2.48–2.25(m,2H).13CNMR(125MHz,CDCl3)δ157.10,146.32,141.70,133.88,131.71,128.92,128.13,127.97,127.33,126.59,125.76,118.45,111.15,96.05,69.25,49.72,22.57.
example 8
1a in example 1 is replaced by 1h, other conditions are the same as example 1, and the experimental results are shown in Table 1.
1H NMR(500MHz,CDCl3)δ7.30–7.18(m,1H),7.05(d,J＝8.0Hz,2H),6.97(d,J＝8.0Hz,2H),6.45(d,J＝9.0Hz,3H),6.08(d,J＝10.0Hz,1H),5.05(t,J＝4.1Hz,1H),4.30–4.15(m,2H),2.45–2.27(m,2H),2.25(s,3H).13C NMR(100MHz,CDCl3)δ157.67,143.14,138.10,136.87,133.72,129.28,128.63,128.53,128.17,127.38,125.72,125.33,94.98,69.32,49.56,22.64,21.03.
example 9
1a in example 1 is replaced by 1i, other conditions are the same as example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 2i:
1H NMR(500MHz,CDCl3)δ7.26–7.21(m,1H),7.14(d,J＝8.4Hz,2H),7.04(d,J＝8.4Hz,2H),6.44(dd,J＝11.8,4.8Hz,3H),6.08(d,J＝9.8Hz,1H),5.06(t,J＝4.2Hz,1H),4.24(t,J＝5.1Hz,2H),2.36(dddd,J＝21.9,17.2,12.1,4.7Hz,2H),1.23(s,9H).13C NMR(125MHz,CDCl3)δ157.68,149.78,143.08,137.82,133.61,129.24,128.58,128.03,127.21,125.33,124.58,94.87,49.48,34.28,31.21,22.58.
example 10
1j is used for replacing 1a in example 1, other conditions are the same as example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 2j:
1H NMR(500MHz,CDCl3)δ7.25(dd,J＝5.8,3.2Hz,1H),6.79(s,1H),6.75(s,2H),6.52–6.40(m,3H),6.08(d,J＝9.6Hz,1H),5.06(t,J＝4.1Hz,1H),4.24(h,J＝5.8Hz,2H),2.45–2.27(m,2H),2.21(s,6H).13C NMR(125MHz,CDCl3)δ157.72,143.06,141.08,137.11,133.60,129.24,128.98,128.54,128.06,127.29,125.32,123.52,109.94,94.88,69.25,49.70,22.58,21.33,21.33.
TABLE 1
Claims (3)
1. A process for preparing a polysubstituted cycloheptatriene derivative having the structure shown in formula I:
R1the substituent group is selected from fluorine, chlorine, bromine, methoxy and methyl; r2The substituent group is selected from methoxy, methyl, fluorine, chlorine and bromine; the method is characterized in that N-alkoxy benzamide substances connected with alkynyl and iodobenzene diacetate are added into a reactor, after the reaction is completed in a solvent by stirring, a rotary evaporator is used for concentrating to obtain a crude product, the crude product is separated by silica gel column chromatography to obtain a target product, and the chemical process is shown in a reaction formula II:
2. the preparation method of claim 1, wherein the molar ratio of the substituted N-alkoxy benzamide to the iodobenzene diacetate is 1: 1.2.
3. the method of claim 1, wherein: the solvent is trifluoroethanol, the reaction temperature is room temperature, and the reaction time is 1 min.
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| Title |
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