Efficient and inexpensive synthesis of benzimidazoles and quinoxalines

Synthetic Communications

Volumn 39, Issue 1, 2009, Pages 175-188

  Raju, B China ^a   Theja, N Dharma ^a   Kumar, J Ashok ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

ketoesters; 1,2 diketones; Ammonium salts; Benzimidazoles; OPDA; Quinoxalines

Indexed keywords

1,2 PHENYLENEDIAMINE; 2 (4 METHYLPHENYL) 6 NITRO 1H BENZO[D]IMIDAZOLE; 2 ARYL BENZIMIDAZOLE; 2 METHYL 1H BENZO[D]IMIDAZOLE; 2 METHYL 3 PHENYLQUINOXALINE; 2 METHYL 6 NITRO 1H BENZO[D]IMIDAZOLE; 2 METHYL 6 NITROBENZIMIDAZOLE; 2 METHYL BENZIMIDAZOLE; 2,3 DIPHENYLQUINOXALINE; 2,6 DIMETHYL 1H BENZO[D]IMIDAZOLE; 2,6 DIMETHYLBENZIMIDAZOLE; 4 (5,6 DIMETHYL 1H BENZO[D]IMIDAZOL 2 YL)PHENOL; 6 NITRO 2,3 DIPHENYLQUINOXALINE; AMMONIA; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; BENZIMIDAZOLE DERIVATIVE; CARBONYL DERIVATIVE; DIKETONE; ESTER DERIVATIVE; INORGANIC SALT; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; COST EFFECTIVENESS ANALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ECONOMIC ASPECT; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 57449107891     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802372525     Document Type: Article

References (43)

1. Hasegawa, M.; Nishigaki, N.; Washio, Y.; Kano, K.; Harris, P. A.; Sato, H.; Mori, I.; West, R. I.; Shibahara, M.; Toyoda, H.; Wang, L.; Nolte, R. T.; Veal, J. M.; Cheng, M. Discovery of novel benzimidazoles as potent inhibitors of TIE-2 and VEGFR-2 tyrosine kinase receptors. J. Med. Chem. 2007, 50, 4453.
2. Hranjec, M.; Kralj, M.; Piantanida, I.; Sedic, M.; Suman, L.; Pavelic, K.; Zamola, G. K. Novel cyano and amidino-substituted derivatives of styryl-2-benzimidazoles and benzimidazo[1,2-a]quinolines: Synthesis, photochemical synthesis, DNA, and antitumor evaluation, part 3. J. Med. Chem. 2007, 50, 5696.
3. A agonists. Eur. J. Med. Chem. 2006, 41, 985.
4. Lopez, M. L. R.; Benhamu, B.; Morcillio, M. J.; Tejada, I. D.; Orensanz, L.; Alfaro, L.; Martin, M. I. Potential antitumor agents 59: Structure-activity relationships for 2-phenylbenzimidazole-4-carboxamides, a new class of minimal DNA-intercalating agents which may not act via topoisomerase II. J. Med. Chem. 1999, 33, 814.
5. Dell, A.; William, D. H.; Morris, H. R.; Smith, G. A.; Feeney, J.; Roberts, G. C. Structure revision of the antibiotic echinomycin. J. Am. Chem. Soc. 1975, 97, 2497.
6. (a) Phillips, M. A. The formation of 2-substituted benziminazoles. J. Chem. Soc. 1928, 2393;
7. (b) Grimmet, M. R.; Katritzky, A. R.; Rees, C. W. Heterocyclic Chemistry, Pergamon: Oxford, UK, 1984; vol. 5, p. 457.
8. (a) Czarny, A.; Wilson, W. D.; Boykin, D. W. Synthesis of mono-cationic and dicationic analogs of Hoechst 33258. J. Heterocycl. Chem. 1996, 33, 1393;
9. (b) Tidwell, R. R.; Geratz, J. D.; Dann, O.; Volz, G.; Zeh, D.; Loewe. Diarylamidine derivatives with one or both of the aryl moieties consisting of an indole or indole like ring: Inhibitors of arginine specific esteroproteases. J. Med. Chem. 1978, 21, 613;
10. (c) Fairley, T. A.; Tidwell, R. R.; Donkor, I.; Naiman, N. A.; Ohemengm, K. A.; Lombardy, R. J.; Bentley, J. A.; Cory, M. Structure, DNA minor groove binding, and base pair specificity of alkyl and aryl linked bis(aminobenzimidazoles) and bis(amidinoindoles). J. Med. Chem. 1993, 36, 1746;
11. (d) Heravi, M. M.; Sadjadi, S.; Oskooie, H. A.; Shoar, R. H.; Bamoharram, F. Heteropolyacids as heterogeneous and recyclable catalysts for the synthesis of benzimidazoles. Catal. Commun. 2008, 9, 504.
12. Brown, D. J. Quinoxalines: Supplements II. In The Chemistry of Heterocyclic Compounds; E. C. Tayler, P. Wipf (Eds.); John Wiley and Sons: NJ, 2004.
13. (a) Sylvain, A.; Elisabet, D. Direct and catalytic synthesis of quinoxaline derivatives from epoxides and ene-1,2-diamines. Tetrahedron Lett. 2002, 43, 3971
14. (b) Jose, B.; Fernando, A.; Romon, L.; Maria-Paz, C. One-pot synthesis of quinoxalines and 2,3-dihydropyrazines via oxidative aminomercuriation of propargyl alcohols. Synthesis 1985, 313;
15. (c) Steven, A. R.; Cecilia, D. W.; Richard, J. K. T. Preparation of quinoxalines, dihydropyrazines, and piperazines using tandem oxidation processes. Chem. Commun. 2003, 2286;
16. (d) Shyamaprasad, G.; Avijit, K. A. A novel one-pot two component synthesis of tricyclic pyrano[2,3b]quinoxalines. Tetrahedron Lett. 2005, 46, 221;
17. (e) Yoram, C.; Amatzya, Y. M.; Mordecai, R. New polyheterocyclic 4n.pi-electron dianions: Paratropocity, charge delocalization, and reactions. J. Am. Chem. Soc. 1986, 108, 7039;
18. (f) Xekoulotakis, N. P.; Hadjiantoniou, M.; Maroulis, A. J. Synthesis of quinoxalines by cyclization of α-arylamino oximes of α-dicarbonyl compounds. Tetrahedron Lett. 2000, 41, 10299;
19. (g) Venu Gopal, K.; Subrahmanyam, M. Single-step synthesis of 2-methylquinoxaline from 1,2-phenylenediamine and 1,2-propanediol over modified HY zeolites. Catal. Commun. 2001, 2, 219.
20. (a) Shyamaprasad, G.; Avijit, K. A. The first microwave-assisted regio-specific synthesis of 6-substituted pterins. Tetrahedron Lett. 2002, 43, 8371;
21. (b) Zhijian, Z.; David, D. W.; Scoot, E. W.; William, H. L.; Craig, W. L. General microwave-assisted protocols for the expedient synthesis of quinoxalines and heterocyclic pyrazines. Tetrahedron Lett. 2004, 45, 4873.
22. (a) Zemin, W.; Nicholas, J. E. Solid-phase synthesis of quinoxalines on Synphase™ lanterns. Tetrahedron Lett. 2001, 42, 8115
23. (b) Orazio, A. A.; Licia, D. C.; Paolino, F.; Fabio, M.; Stefania, S. Improved synthesis of substituted quinoxalines from new N/N-polymer-bound 1,2-diaza-1,3-butadienes. Synlett 2003, 1183.
24. More, S. V.; Sastry, M. N. V.; Wang, C.-C.; Yao, C. Molecular iodine: A powerful catalyst for the easy and efficient synthesis of quinoxalines. Tetrahedron Lett. 2005, 46, 6345.
25. Darabi, H. R.; Mohandessi, S.; Aghapoor, K.; Mohsenzadeh, F. A recyclable and highly effective sulfamic acid/MeOH catalytic system for the synthesis of quinoxalines at room temperature. Catal. Commun. 2007, 8, 389.
26. (a) Shaabani, A.; Bazir, A.; Teimouri, F.Ammoniumchloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions. Tetrahedron Lett. 2003, 44, 857
27. (b) Tanemura, K.; Suzuki, T.; Nishida, Y.; Satsumabayashi, K.; Horaguchi, T. Halogenation of aromatic compounds by N-chloro, N-bromo, and N-iodosuccinimide. Chem. Lett. 2003, 32, 932.
28. (a) Gangadasu, B.; Narender, P.; Ramesh, C.; China Raju, B.; Rao, V. J. Facile and selective synthesis of chloronicotinaldehydes by the Vilmeier reaction. Tetrahedron 2006, 62, 8398
29. (b) China Raju, B.; Neelakantan, P.; Bhalerao, U. T. Quinone methide initiated cyclization reaction: Synthesis of 4-aryl-1,2,3,4- tetrahydroisoquinolines. Tetrahedron Lett. 2004, 45, 7487
30. (c) Gangadasu, B.; China Raju, B.; Rao, V. J. A simple and convenient preparation of 2-chloro-5-methylpyridine-3-carbaldehydeimines. Heterocycl. Commun. 2002, 8, 243.
31. (a) Narender, P.; Gangadasu, B.; Ramesh, C.; China Raju, B.; Rao, V. J. Facile and selective synthesis of chloromethylpyridines and chloropyridines using diphosgene/triphosgene. Synth. Commun. 2004, 34, 1097
32. 4. Tetrahedron Lett. 2003, 44, 2525;
33. (c) Babu, K. S.; China Raju, B.; Srinivas, P. V.; Rao, A. S.; Kumar, S. P.; Rao, J. M. A simple, effective, and highly selective cleavage of 3-methylbut-2-enyl(prenyl) ethers using p-toluenesulfonic acid. Chem. Lett. 2003, 32, 704.
34. Latif, N.; Mishriky, N.; Assad, F. M.; Meguid, S. B. β-Nitrostyrenes with o-phenylenediamine: A new route of the synthesis of 2-substituted benzimidazoles. Indian J. Chem. 1982, 21B, 872.
35. Bougrin, K.; Soufiaoui, M. Nouvelle voie de synthese des arylimidazoles sous irradiation micro-ondes en milieusec. Tetrahedron Lett. 1995, 36, 3683.
36. Matsushita, H.; Lee, S.-H.; Joung, M.; Clapham, B.; Janda, K. D. Smart cleavage reactions: The synthesis of benzimidazoles and benzothiazoles from polymer-bound esters. Tetrahedron Lett. 2004, 45, 313.
37. Kim, J. S.; Sun, Q.; Gatto, B. G.; Yu, C.; Liu, A.; Liu, L. F.; Lavoie, E. J. Structure-activity relationships of benzimidazoles and related heterocycles as topoisomerase I poisons. Bioorg. Med. Chem. 1996, 4, 621.
38. Valdez, J.; Cedillo, R.; Hernandez-Campos, A.; Yepez, L.; Hernandez-Luis, F.; Nararrete-Vazquez, G.; Tapia, A.; Cortes, R.; Hernandez, M.; Castillo, R. Bioorg. Med. Chem Lett. 2002, 12, 2221.
39. Mallory, F. B.; Wood, C. S.; Hurwitz, B. M. Furazan oxides IV: Extentions of the scope of the haloalkoxy substitution reaction. J. Org. Chem. 1964, 29, 2605.
40. Von Siegrist, A. E. Umberein neve synthese zur darstellung heterocyclish substituierter stilbene ver bindungen die anil-synthese. Helvetica Chim. Acta 1967, 50, 906.
41. Liu, J. H.; Wu, A. T.; Huang, M.-H.; Wu, C.-W.; Chung, W.-S. The synthesis of pyrazino-containing sultins and their application in Diels-Alder reactions with electron poor olefins and [60]fullerene. J. Org. Chem. 2000, 65, 3395.
42. Ainscow, T. A.; Belmont, M. R.; Henshall, J. L.; Hooper, R. M.; Simmonds, D. J. Synthesis of four n-alkanes with terminal dipolar substitutents. Tetrahedron 1987, 43, 115.
43. Kwon, H. B.; McKee, B. H.; Stille, J. K. Palladium-catalyzed coupling reactions of (alpha-ethoxyvinyl) trimethylstannane with vinyl and aryl triflates. J. Org. Chem. 1990, 55, 3114.