Heteroaromatic annulation of 2-methyl/2-cyanomethylbenzimidazole dianions with α-oxoketene dithioacetals: A highly regioselective synthetic protocol for 1,2-and 2,3-substituted/annulated pyrido[1,2-a]benzimidazoles

Journal of Organic Chemistry

Volumn 68, Issue 9, 2003, Pages 3498-3506

  Panda, Kausik ^a   Suresh, J R ^a   Ila, H ^a   Junjappa, H ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROAROMATIC ANNULATION;

CONDENSATION; NEGATIVE IONS; PHOSPHORIC ACID;

ORGANIC COMPOUNDS;

1 (METHYLTHIO) 3 PHENYLPYRIDO[1,2 A]BENZIMIDAZOLE; 12 METHYLTHIO 1,2,3,4 TETRAHYDROBENZIMIDAZO[1,2 B]ISOQUINOLINE; 12 METHYLTHIO 2,3 CYCLOHEXAPYRIDO[1,2 A]BENZIMIDAZOLE; 14 (METHYLTHIO)BENZIMIDAZO[1,2 F]FLUORANTHENE; 2 CYANOMETHYLBENZIMIDAZOLE; 2 METHYLBENZIMIDAZOLE; 2,3 CYCLOPENTAPYRIDO[1,2 A]BENZIMIDAZOLE; 2,3 DIMETHYL 1 (METHYLTHIO)PYRIDO[1,2 A]BENZIMIDAZOLE; 3 BIS(METHYLTHIO)ACENAPHTHEN 1 ONE; 3 METHYL 1 (METHYLTHIO)PYRIDO[1,2 A]BENZIMIDAZOLE; 4 BIS(METHYLTHIO) 3 BUTEN 2 ONE; 4 CYANO 1 METHYL 3 (METHYLTHIO)PYRIDO[1,2 A]BENZIMIDAZOLE; 4 CYANO 3 METHYLTHIO 1 PHENYLPYRIDO[1,2 A]BENZIMIDAZOLE; 5,6 DIHYDRO 7 (METHYLTHIO)BENZIMIDAZO[1,2 B]BENZO[F]ISOQUINOLINE; 6 CYANO 5 METHYLTHIO 1,2,3,4 TETRAHYDROBENZIMIDAZO[1,2 A]QUINOLINE; 8 CYANO 5,6 DIHYDRO 7 (METHYLTHIO)BENZIMIDAZO[1,2 A]BENZO[H]QUINOLINE; 8 CYANO 7 (METHYLTHIO)BENZIMIDAZO[1,2 E]FLUORANTHENE; ACETAL DERIVATIVE; ALPHA OXOKETENE; ANION; BENZIMIDAZOLE DERIVATIVE; KETENE DERIVATIVE; KETENE DITHIOACETAL; KETONE; METHANOL; PHOSPHORIC ACID; POLYCYCLIC HYDROCARBON; UNCLASSIFIED DRUG;

ANNULATION; ARTICLE; CHEMICAL REACTION; CONJUGATION; CRYSTAL STRUCTURE; CYCLOADDITION; POLYMERIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037414494     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026786w     Document Type: Article

References (65)

1. Chezal, J. M.; Moreau, E.; Delmas, G.; Gueiffier, A.; Blache, Y.; Grassy, G.; Lartigue, C.; Chavignon, O.; Teulade, J. C. J. Org. Chem. 2001, 66, 6576 and references therein.
2. (a) Barun, O.; Ila, H.; Junjappa, H.; Singh, O. M. J Org. Chem. 2000, 65, 1583 and references therein.
3. (b) Almirante, L.; Polo, L.; Mugnaini, A.; Provinciali, E.; Rugarli, P.; Biancotti, A.; Gamba, A.; Murmann, W. J. Med. Chem. 1965, 8, 305.
4. (c) Yamamoto, T.; Tsuji, K.; Kosuge, T.; Okamoto, T.; Shudo, K.; Takeda, K.; Itaka, Y.; Yamaguchi, K.; Seino, Y.; Yahagi, T.; Nagao, M.; Sugimura, T. Proc. Jpn. Acad. B 1978, 54, 248.
5. (d) Davey, D.; Erhardt, P. W.; Lumma, W. C., Jr.; Wiggins, J.; Sullivan, M.; Pang, D.; Cantor, E. J. Med. Chem. 1987, 30, 1337.
6. (e) Kaminski, J. J.; Hilbert, J. M.; Pramanik, B. N.; Solomon, D. M.; Conn, D. J.; Rizvi, R. K.; Elliott, A. J.; Guzik, H.; Lovey, R. G.; Domalski, M. S.; Wong, S. C.; Puchalski, C.; Gold, E. H.; Long, J. F.; Chiu, P. J. S.; McPhail, A. J. Med. Chem. 1987, 30, 2031.
7. (f) Kaminski, J. J.; Perkins, D. J.; Frantz, J. D.; Solomon, D. M.; Elliot, A. J.; Chiu, P. J.; Long, J. F. J. Med. Chem. 1987, 30, 2047.
8. (g) Spitzer, W. A.; Victor, F.; Pollock, G. D.; Hayes, J. S. J. Med. Chem. 1988, 31, 1590.
9. (a) Molina, P.; Alajarin, M.; Vidal. A. J. Org. Chem. 1992, 57, 6703 and references therein.
10. (b) Chavignon, O.; Teulade, J. C.; Roche, D.; Madesclaire, M.; Blache, Y.; Gueiffier, A.; Chabard, J. L.; Dauphin, G. J. Org. Chem. 1994, 59, 6413.
11. (c) Chezal, J. M.; Delmas, G.; Mavel, S.; Elhakmaoui, H.; Metin, J.; Diez, A.; Blache, Y.; Gueiffier, A.; Rubiralta, M.; Teulade, J. C.; Chavignon, O. J. Org. Chem. 1997, 62, 4085.
12. (d) Takahashi, T.; Shibasaki, J. J. Pharm. Soc. Jpn. 1949, 69, 496.
13. (e) Almirante, L.; Mugnaini, A.; De Toma, N.; Murmann, W. Boll. Chim. Farm. 1971, 110, 322.
14. (f) Rees, C. W.; Smith, D. J. Chem. Soc., Perkin Trans. 1 1987, 1159.
15. (a) Henn, L.; Hickey, D. M. B.; Moody, C. J.; Rees, C. W. J. Chem. Soc., Perkin Trans. 1 1984, 2189.
16. (b) Hickey, D. M. B.; Moody, C. J.; Rees, C. W. J. Chem. Soc., Perkin Trans. 1 1986, 1119.
17. (c) Ning, R. Y.; Blount, J. F.; Madan, P. B.; Fryer, R. I. J. Org. Chem. 1977, 42, 1791.
18. (d) Takamura, T.; Chiba, T.; Tejima, S. Chem. Pharm. Bull. 1978, 26, 2924.
19. (e) Saint-Ruf, G.; Loukakou, B.; Nzouzi, C. J. Heterocycl. Chem. 1981, 18, 1565.
20. (f) Hashimoto, Y.; Shudo, K.; Okamoto, T. J. Am. Chem. Soc. 1982, 104, 7637.
21. (g) Bohacek, R.; De Lombaert, S.; McMartin, C.; Priestle, J.; Grutter, M. J. Am. Chem. Soc. 1996, 118, 8231.
22. (a) Morgan, G.; Stewart, J. J. Chem. Soc. 1938, 1292.
23. (b) Morgan, G.; Stewart, J. J Chem. Soc. 1939, 1057.
24. (a) Bogdanowicz-Szwed, K.; Czarny, A. J. Prackt. Chem. 1993, 335, 279.
25. (b) Toth, G.; Kovacs, A.; Balogh, M.; Hermecz, I. J. Heterocycl. Chem. 1991, 28, 497.
26. (a) Pastor, J.; Siro, J. G.; Garcia-Navio, J. L.; Vaquero, J. J.; Rodrigo, M. M.; Ballesteros, M.; Alvarez-Builla. J. Biorg. Med. Chem. Lett. 1995, 5, 3043.
27. (b) Postor, J.; Siro, J. G.; Garcia-Navio, J. L.; Vaquero, J. J.; Alvarez-Builla, J.; Gago, F.; de Pascual-Teresa, B.; Pastor, M.; Rodrigo, M. M. J. Org. Chem. 1997, 62, 5476.
28. (c) Feigon, J.; Denny, W. A.; Leupin, W.; Kearns, D. R. J. Med. Chem. 1984, 27, 450.
29. (a) Koenigsmann, M.; Zafferani, M.; Danhauser-Rield, S.; Reuti, B.; Houlihan, W. J.; Thiel, E.; Berdel, W. E. Cancer Lett. 1992, 67, 145.
30. (b) Brana, M. F.; Castellano, J. M.; Keilhauer, G.; Machuca, A.; Martin, Y.; Redondo, C.; Schlick, E.; Walker, N. Anticancer Drug Res. 1994, 9, 527.
31. (a) Bangar, R. B.; Varadarajan, T. S. Appl. Phys. B: Lasers Opt. 1994, B58, 79.
32. (b) Bangar, R. B.; Varadarajan, T. S. Spectrosc. Lett. 1993, 26, 1953.
33. (a) Knolker, H. J.; Boese, R.; Hitzemann, R. Chem. Ber. 1990, 123, 327.
34. (b) Ohta, S.; Yuasa, T.; Narita, Y.; Kawasaki, I.; Minamii, E.; Yamashita, M. Heterocycles 1991, 32, 1923.
35. (c) Schaefer, H.; Gruner, M.; Grossmann, G.; Gewald, K. Monatsh. Chem. 1991, 122, 959.
36. (a) Tennant, G. In The Chemistry of Heterocyclic Compunds; Weissberger, A., Taylor, E. C., Eds.; Interscience Publishers: New York, 1980; Vol. 40, Part 2, p 257.
37. (b) Mosby, W. L. In The Chemistry of Heterocyclic Compunds; Weissberger, A., Taylor, E. C., Eds.; Interscience Publishers: New York, 1961; Vol. 15, p 507.
38. Fletcher, N. C.; Abeln, D.; von Zelewsky, A. J. Org. Chem. 1997, 62, 8577.
39. (a) Alajarin, M.; Vidal, A.; Tovar, F. Tetrahedron Lett. 2000, 41, 7029.
40. (b) Alajarin, M.; Vidal, A.; Tovar, F.; Conesa, C. Tetrahedron Lett. 1999, 40, 6127.
41. (a) Ila, H.; Junjappa, H.; Mohanta, P. K. In Progress in Heterocyclic Chemistry; Gribble, G. W., Gilchrist, T. L., Eds.; Pergamon Press: Oxford, UK, 2001; Vol. 13, Chapter 1, p 1.
42. (b) Junjappa, H.; Ila, H.; Patro, B.; Rao, Ch. S. J. Indian Chem Soc. 1994, 71, 501.
43. (a) Suresh, J. R.; Syam Kumar, U. K.; Ila, H.; Junjappa, H. Tetrahedron 2001, 57, 781.
44. (b) Suresh, J. R.; Barun, O.; Ila, H.; Junjappa, H. Tetrahedron 2000, 56, 8153.
45. (c) Barun, O.; Patra, P. K.; Ila, H.; Junjappa, H. Tetrahedron Lett. 1999, 40, 3797.
46. (d) Basaveswara Rao, M. V.; Syam Kumar, U. K.; Ila, H.; Junjappa, H. Tetrahedron 1999, 55, 11563.
47. (e) Kishore, K.; Reddy, K. R.; Suresh, J. R.; Ila, H.; Junjappa, H. Tetrahedron. 1999, 55, 7645.
48. (f) Patra, P. K.; Suresh, J. R.; Ila, H.; Junjappa, H. Tetrahedron 1998, 54, 10167.
49. (g) Syam Kumar, U. K.; Patra, P. K.; Ila, H.; Junjappa, H. Tetrahedron Lett. 1998, 39, 2029.
50. (h) Suresh, J. R.; Patra, P. K.; Ila, H.; Junjappa, H. Tetrahedron 1997, 53, 14737.
51. (i) Patra, P. K.; Suresh, J. R.; Ila, H.; Junjappa, H. Tetrahedron Lett. 1997, 38, 3119.
52. (j) Reddy, K. R.; Roy, A.; Ila, H.; Junjappa, H. Tetrahedron 1995, 51, 10941.
53. (k) Roy, A.; Nandi, S.; Ila, H.; Junjappa, H. Org. Lett. 2001, 3, 229.
54. (l) Satyanarayana, J.; Reddy, K. R.; Ila, H.; Junjappa. H. Tetrahedron Lett. 1992, 33, 6173.
55. (m) Reddy, K. R.; Ila, H.; Junjappa, H. Synthesis 1995, 929.
56. (n) Balu, M. P.; Pooranchand, D.; Ila, H.; Junjappa, H. Tetrahedron Lett. 1988, 29, 501.
57. (o) Pooranchand, D.; Satyaranayana, J.; Ila, H.; Junjappa, H. Synthesis. 1993, 241.
58. 1H NMR spectra of all the newly synthesized 1-phenylpyrido[1,2-α]benzimidazole 6a, 6d, and 11-12a displayed a higher field shift of the H-9 proton (σ 5.92-6.44) due to the shielding effect of the 1-phenyl group.
59. 13C NMR spectral data.
60. (a) Olson, C. E.; Bader, A. R. Org. Synth. 1955, 35, 95-96.
61. (b) Arcus, C. L.; Barett, G. C. J. Chem. Soc. 1958, 2740.
62. (c) Fieser, F J. Am. Chem. Soc. 1940, 62, 432.
63. (d) Vogel, A. I. Textbook of Organic Chemistry, 5th ed.; ELBS: London, UK, 1988; p 1162.
64. (e) Copeland, R. A. B.; Day, A. R. J. Org. Chem. 1943, 65, 1072.
65. (f) Chauhan, S. M. S.; Junjappa, H. Tetrahedron 1976, 32, 1779.