CN103254108B - Preparation method of multifunctional pyrrole and pyrrolo [3,4-C ] quinoline - Google Patents
Preparation method of multifunctional pyrrole and pyrrolo [3,4-C ] quinoline Download PDFInfo
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- CN103254108B CN103254108B CN201210267830.1A CN201210267830A CN103254108B CN 103254108 B CN103254108 B CN 103254108B CN 201210267830 A CN201210267830 A CN 201210267830A CN 103254108 B CN103254108 B CN 103254108B
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- HNMHAFWWHHBJPC-UHFFFAOYSA-N 2h-pyrrolo[3,4-c]quinoline Chemical compound C1=CC=C2C3=CNC=C3C=NC2=C1 HNMHAFWWHHBJPC-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 11
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 8
- -1 3, 4-disubstituted pyrrole compounds Chemical class 0.000 claims abstract description 6
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 claims abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 230000008030 elimination Effects 0.000 claims description 6
- 238000003379 elimination reaction Methods 0.000 claims description 6
- 235000019441 ethanol Nutrition 0.000 claims description 6
- 239000005457 ice water Substances 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 238000010898 silica gel chromatography Methods 0.000 claims description 6
- 238000010025 steaming Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 10
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000002474 experimental method Methods 0.000 abstract description 2
- BLGXIWMWVDNMJL-UHFFFAOYSA-N CC(=O)C.N1C(=O)C(=O)C2=CC=CC=C12 Chemical compound CC(=O)C.N1C(=O)C(=O)C2=CC=CC=C12 BLGXIWMWVDNMJL-UHFFFAOYSA-N 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000003233 pyrroles Chemical class 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000006352 cycloaddition reaction Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- BSUNEUGPXRSCLF-UHFFFAOYSA-N 3h-pyrrolo[2,3-c]quinoline Chemical compound C1=CC=C2C(C=CN3)=C3C=NC2=C1 BSUNEUGPXRSCLF-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 238000006086 Paal-Knorr synthesis reaction Methods 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006452 multicomponent reaction Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 201000000498 stomach carcinoma Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a novel preparation method of multifunctional pyrrole and pyrrolo [3,4-C ] quinoline, wherein the multifunctional pyrrole is generated by a one-step method by using various condensation products of TOSMIC and isatin methyl ketone in a reaction system taking liquid alcohol as a solvent, and the solvent also participates in the reaction; pyrrolo [3,4-C ] quinolines are further produced by dehydration of the multifunctional pyrrole by means of phosphorus oxychloride. The method has the advantages of mild reaction conditions, short reaction time, simple experimental operation, easy preparation of raw materials and convenient post-treatment of experiments; 3, 4-disubstituted pyrrole compounds are synthesized by a one-step method, pyrrolo [3,4-C ] quinoline compounds are synthesized by a simple method, and the yield is high.
Description
Technical field
The present invention relates to technical field of chemistry, specifically, is the new preparation process of a kind of multifunctional pyrrole and pyrrolo-[3,4-C] quinoline.
Background technology
Multifunction pyrroles is present in some natural product widely; medicament production and central (T. L. Gilchrist, J. Chem. Soc. Perkin Trans. 1 2001, the 2491 – 2515. G. Murineddu of agrochemicals; G. Loriga; E. Gavini, A. T.Peanna, A. C. Mule; G. A. Pinna; Arch. Pharm. Med.Chem. 2001,334,393 – 398; H. Z. Walter, Z. Naturforsch. B 2008,63; 351 – 362.); simultaneously also be found in the preparation of organic semiconductor material, photodiode and solar cell multifunction pyrroles in recent years have a wide range of applications (C. F. Lee, L. M. Yang, T. Y. Hwu; A. S. Feng; J. C.Tseng, T. Y. Luh, J. Am. Chem. Soc. 2000; 122,4992 – 4993; A. Kreutzberger, P. A. Kalter, J. Org. Chem.1960,25,554.).From having document at present; the most classical method for the synthesis of pyrroles comprises Knorr and reacts (L. Knorr; H. Lange; Ber. Dtsch. Chem. Ges.1902; 35,2998 – 3009.), Paal-Knorr reacts (L. Knorr, Ber. Dtsch. Chem. Ges.1885; 18,299 – 231; C. Paal, Ber. Dtsch. Chem. Ges.1885,18,367 – 371.), Hantzsch reacts (A. Hantzsch, Ber. Dtsch.Chem. Ges. 1890,23,1474 – 1476.).Also has some cycloaddition reactions (Y. Kim, J. Kim, S. B. Park in addition, Org. Lett.2009,11,17 – 20.) and transition metal-catalyzed cyclization (A. Saito, O. Konishi, Y. Hanzawa, Org. Lett. 2010,12,372 – 374 .) and multi-component reaction (V. Estvez, M. Villacampa, J. C. Menndez, Chem. Soc.Rev. 2010,39,4402 – 4421.) be used for synthesizing pyrrole ring.But these methods have certain limitation, as productive rate is low, complex operation etc.It should be noted that the preparation of 3,4-disubstituted pyrroles is particularly difficult, because the electrophilic substitution reaction of most of pyrroles all occurs in α position (Anderson, H. J.; Loader, C. E.; Xu, R. X.; Le, N.; Gogan, N. J.; McDonald, R.; Edwards, L. G.Can. J. Chem. 1985,63,896-902), therefore want that optionally introducing some groups in the β position of pyrroles is more difficult comparatively speaking.
Quino-pyrroles is also very important skeleton structure, and it has a lot of biological activitys, and such as it is present in central (Leach, the C. A. of inhibitor of cancer of the stomach ATP enzyme widely; Brown, T. H.; Ife, R. J.; Keeling, D. J.; Laing, S. M.; Parsons, M. E.; Price, C. A.; Wiggall, K.J. J Med. Chem. 1992,35,1845.), be also skeleton structure (Marquez, the V. E. of some antitumor drugs; Crauston, J. W.; Ruddon, R. W.; Kier, L. B.; Burckhalter, T. H. J Med. Chem. 1972,15,36.).The synthesis of quino-pyrroles also once reported by some documents, comprised by thermal cyclization reaction (Kim, S.S.; Cheon, H. G.; Kang, S.K.; Yum, E. K.; Choi. J.-IC Heterocycles.1998,48,221.), cycloaddition reaction (Martin, the S. F. of 1,3-dipole in molecule; Cheavens. T. H. Tetrahedron Lett. 1989,30,7017.), Diels-Alder reacts (Hadden, M.; Stevenson, P. J. Tetrahedron Lett. 1999,40,1215.) etc.But these reaction normal yields are all lower, and the limitation of functional group is larger, simultaneously the preparation also more complicated of raw material, and report at present many be synthesis (the Seung Kyu Kang of the compound of pyrrolo-[2,3-c] quinoline; Sang Sun Park; Sung Soo Kim; Joong-Kwon Choi; Eul Kgun Yum.Tetrahedron Lett. 1999,40,4379-4382), and then considerably less for the report of this kind of pyrrolo-[3,4-c] quinoline, and its synthesis is also relatively difficult, usually needs more step.
Therefore this kind of multifunction 3,4-disubstituted pyrroles and pyrrolo-[3,4-c] synthesis of quinoline is a part more difficult in organic synthesis field always, also be the hot fields of organic synthesis and pharmaceutical chemistry research simultaneously, and the skeleton framework that it can provide some basic for the synthesis of some medicines, has potential biological activity.
Summary of the invention
The object of the invention is to the above problem overcoming prior art existence, provide the new preparation process of a kind of multifunctional pyrrole and pyrrolo-[3,4-C] quinoline, experimental implementation is simple, and raw material preparation easily, tests convenient post-treatment, and completed by single stage method, productive rate is high.
For realizing above-mentioned technical purpose, reach above-mentioned technique effect, the present invention is achieved through the following technical solutions:
The new preparation process of multifunctional pyrrole and pyrrolo-[3,4-C] quinoline, comprises the following steps:
Step 1) adds 3-(2-oxo-2-phenyl-ethylene) isatin-2 ketone, TOSMIC and t-KOBu in round-bottomed flask, be cooled to 0 DEG C, anhydrous methanol is added under the condition of ice-water bath, finish, continue to stir 10 minutes at 0 DEG C, removing ice-water bath continues complete in stirring at room temperature 3h, TLC detection reaction;
Step 2) reaction terminate after, solvent is spin-dried for, adds appropriate water, then use dichloromethane extraction, merge organic layer, with anhydrous sodium sulfate drying, after elimination siccative, pressure reducing and steaming solvent, obtain product by silica gel column chromatography, then obtain the crystal of white with ethyl alcohol recrystallization, i.e. multifunctional pyrrole;
Step 3) slowly drips steamed phosphorus oxychloride add described multifunctional pyrrole, anhydrous CH3CN nitrogen protection in round-bottomed flask under, and this reaction under reflux conditions stirs 10h, and TLC detection reaction is complete;
After step 4) reaction terminates, be cooled to room temperature, add water dilution, with the NaOH of 10%, pH is adjusted to 8, then is extracted with ethyl acetate; Merge organic layer, with anhydrous sodium sulfate drying, after elimination siccative, pressure reducing and steaming solvent; Silica gel column chromatography is separated to obtain product, then obtains tan crystals with ethyl alcohol recrystallization, i.e. pyrrolo-[3,4-C] quinoline.
The technological reaction formula of synthesizing described multifunctional pyrrole and described pyrrolo-[3,4-C] quinoline is:
Compared with prior art, the present invention has the following advantages:
1, reaction conditions of the present invention is gentle, and the time is fast, and experimental implementation is simple, and raw material preparation is easy, experiment convenient post-treatment;
2, the present invention passes through one-step synthesis method 3,4-disubstituted pyrroles compounds and synthesizes pyrrolo-[3,4-C] quinolines by simple method, and productive rate is high.
Above-mentioned explanation is only the general introduction of technical solution of the present invention, in order to better understand technique means of the present invention, and can be implemented according to the content of specification sheets, be described in detail as follows below with preferred embodiment of the present invention.
Embodiment
Below in conjunction with embodiment, describe the present invention in detail.
The new preparation process of multifunctional pyrrole and pyrrolo-[3,4-C] quinoline, comprises the following steps:
Step 1) adds the t-KOBu of 3-(2-oxo-2-phenyl-ethylene) isatin-2 ketone of 0.5mmol, TOSMIC and 1.5mmol of 0.6mmol in 10 mL round-bottomed flasks, be cooled to 0 DEG C, 2ml anhydrous methanol is added under the condition of ice-water bath, finish, continue to stir ten minutes at 0 DEG C, removing ice-water bath continues complete in stirring at room temperature 3h, TLC detection reaction;
Step 2) reaction terminate after, solvent is spin-dried for, add appropriate water, then use the dichloromethane extraction of 3 × 20 mL, merge organic layer, with anhydrous sodium sulfate drying, after elimination siccative, pressure reducing and steaming solvent, obtains product by silica gel column chromatography, the crystal of white is obtained again, i.e. multifunctional pyrrole with ethyl alcohol recrystallization;
Step 3) slowly drips the steamed phosphorus oxychloride of 5mmol add the anhydrous CH3CN nitrogen protection of the described multifunctional pyrrole of 0.5 mmol, 10 mL in 20 mL round-bottomed flasks under, this reaction under reflux conditions stirs 10h, and TLC detection reaction is complete;
After step 4) reaction terminates, be cooled to room temperature, add the water dilution of 10ml, with the NaOH of 10%, pH is adjusted to 8, then uses the extraction into ethyl acetate of 3 × 20mL; Merge organic layer, with anhydrous sodium sulfate drying, after elimination siccative, pressure reducing and steaming solvent; Silica gel column chromatography [eluent V(acetone): V(sherwood oil)=1:4] be separated to obtain product, then obtain tan crystals with ethyl alcohol recrystallization, i.e. pyrrolo-[3,4-C] quinoline.
The technological reaction formula of synthesizing described multifunctional pyrrole and described pyrrolo-[3,4-C] quinoline is:
The foregoing is only the preferred embodiments of the present invention, be not limited to the present invention, for a person skilled in the art, the present invention can have various modifications and variations.Within the spirit and principles in the present invention all, any amendment done, equivalent replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (1)
1. the preparation method of pyrrolo-[3,4-c] quinoline, is characterized in that, described preparation method's step is as follows:
Step 1, to add in round-bottomed flask in 3-(2-oxo-2-phenyl-ethylene) isatin-2 ketone (in reaction formula for 1a), TOSMIC(reaction formula be 2a) and t-KOBu, be cooled to 0 DEG C, anhydrous methanol is added under the condition of ice-water bath, finish, continue to stir ten minutes at 0 DEG C, removing ice-water bath continues complete in stirring at room temperature 3h, TLC detection reaction;
After step 2, reaction terminate, solvent is spin-dried for, adds appropriate water, then use dichloromethane extraction, merge organic layer, with anhydrous sodium sulfate drying, after elimination siccative, pressure reducing and steaming solvent, product is obtained by silica gel column chromatography, obtaining the crystal of white again with ethyl alcohol recrystallization, is 3,4-disubstituted pyrroles (being 3a in reaction formula);
Step 3, in round-bottomed flask, add 3,4-disubstituted pyrroles (being 3a in reaction formula), anhydrous CH
3slowly drip steamed phosphorus oxychloride under CN nitrogen protection, this reaction under reflux conditions stirs 10h, and TLC detection reaction is complete;
After step 4, reaction terminate, be cooled to room temperature, thin up, with the NaOH of 10%, pH be adjusted to 8, then be extracted with ethyl acetate; Merge organic layer, with anhydrous sodium sulfate drying, after elimination siccative, pressure reducing and steaming solvent, silica gel column chromatography is separated to obtain product, then obtains tan crystals with ethyl alcohol recrystallization, i.e. pyrrolo-[3,4-c] quinoline (being 4a in reaction formula);
The reaction formula of above-mentioned preparation method is as follows:
；
。
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Non-Patent Citations (2)
| Title |
|---|
| 《Cyclisierung von Phenylhydrazonen substituierter Pyrrol-3-aldehyde zu 2H-Pyrrolo[3.4-c]chinolinen》;von Helmut Fritz et al.;《Liebigs Ann. Chem.》;19721231;第762卷;第121－126页 * |
| 《Reversible Inhibitors of the Gastric (H+/K+)-ATPase. 2.》;Colin A. Leach et al.;《J. Med. Chem.》;19821231;第35卷(第10期);1845-1852 * |
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