An unprecedented and concise method for the synthesis of 1,3-thiazino-[3,4a][1,3]benzimidazoles via a three-component reaction

Synlett

Volumn , Issue 10, 2010, Pages 1469-1472

  Alizadeh, Abdolali ^a   Noaparast, Zohreh ^a   Sabahnoo, Hamideh ^a   Zohreh, Nasrin ^a  

^a TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

1,3 thiazine; Aryl isothiocyanate; Benzimidazole; Methyl propiolate; Multicomponent reaction; O phenylenediamine; Thiazinobenzimidazole

Indexed keywords

ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; BENZIMIDAZOLE DERIVATIVE; CARBON; DICHLOROMETHANE; ISOTHIOCYANIC ACID; N ARYL N [1,3]THIAZINO[3,4 A][1,3]BENZIMIDAZOL 1 YLIDENEAMINE; PHENYLENEDIAMINE; TOLUENE; UNCLASSIFIED DRUG;

ACCURACY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 77953273922     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219934     Document Type: Article

References (41)

1. Patel H S., Patel N P., Orient. J. Chem. 1997 13 69
2. Madkour H M. F., Salem M A. I., Soliman E A., Mahmoud N F. H., Phosphorus, Sulfur Silicon Relat. Elem. 2001 170 15
3. Ingarsal N, Amutha P, Nagarajan S, [nl]J. Sulfur Chem. 2006 27 455
4. Tozkoparan B, Aktay G, Yeilada E, Farmaco 2002 57 145
5. Barret G C., Kane V V., Lowe G, J. Chem. Soc. 1964 783
6. Patani G A., LaVoie E, J. Chem. Rev. 1996 96 3147
7. Schmidt R R., Synthesis 1972 333
8. BernalteGarc A, GarcBarros F J., HigesRolando F J., LunaGiles F, PedreroMar R, J. Inorg. Biochem. 2004 98 15
9. Orjales A, Mosquera R, Labeaga L, Rodes R, [nl]J. Med. Chem. 1997 40 586
10. Grimmett M R., Comprehensive Heterocyclic Chemistry II Vol. 3 Katritzky A R. Rees C W. Scriven E F. Elsevier Oxford 1996 77
11. Labanauskas L K., Brukstus A B., Gaidelis P G., Buchinskaite V A., Udrenaite E B., Dauksas V K., Pharm. Chem. J. 2000 34 353
12. Ishida T, Suzuki T, Hirashima S, Mizutani K, Yoshida A, Ando I, Ikeda S, Adachi T, Hashimoto H, Bioorg. Med. Chem. Lett. 2006 16 1859
13. Garuti L, Roberti M, Gentilomi G, Farmaco 2001 56 815
14. Iemura R, Kawashima T, Fukuda T, Ito K, Tsukamoto G, J. Med. Chem. 1986 29 1178
15. Venkatesan P, J. Antimicrob. Chemother. 1998 41 145
16. Pawar N S., Dalal D S., Shimpi S R., Mahulikar P P., Eur. J. Pharm. Sci. 2004 21 115
17. Valdez J, Cedillo R, Hernandez-Campos A, Yepez L, Hernandez-Luis F, Navarrete-Vazquez G, Tapia A, Cortes R, Hernandez M, Castillo R, Bioorg. Med. Chem. Lett. 2002 12 2221
18. Mann J, Baron A, Opoku-Boahen Y, Johansson E, Parkinson G, Kelland L R., Neidle S, J. Med. Chem. 2001 44 138
19. Boiani M, Gonzalez M, Mini-Rev. Med. Chem. 2005 5 409
20. Mederski W K. R., Dorsch D, Anzali S, Gleitz J, Cezanne B, Tsaklakidis C, Bioorg. Med. Chem. Lett. 2004 14 3763
21. Kubo K, Kohara Y, Yoshimura Y, Inada Y, Shibouta Y, Furukawa Y, Kato T, Nishikawa K, Naka T, J. Med. Chem. 1993 36 2343
22. Cole E R., Crank G, Salam-Sheikh A, J. Agric. Food Chem. 1974 22 918
23. Ayhan-Kilcigil G, Kus C, oban T, Can-Eke B, Ozbey S, Iscan M, J. Enzyme Inhib. Med. Chem. 2005 20 503
24. Kai H, Morioka Y, Koriyama Y, Okamoto K, Hasegawa Y, Hattori M, Koike K, Chiba H, Shinohara S, Iwamoto Y, Takahashi K, Tanimoto N, Bioorg. Med. Chem. Lett. 2008 18 6444
25. Leflemme N, Dallemagne P, Rault S, Tetrahedron Lett. 2004 45 1503
26. Noshio T, Konno Y, Ori M, Sakamoto M, Eur. J. Org. Chem. 2001 3533
27. Tozkoparan B, Aktay G, Yesilada E, Farmaco 2002 57 145
28. Lamberth C, Querniard F, Tetrahedron Lett. 2008 49 2286
29. Ryabukhin S V., Plaskon A S., Ostapchuk E N., Volochnyuk D M., Shishkin O V., Shivanyuk A N., Tolmachev A A., Org. Lett. 2007 9 4215
30. Middleton R W., Wibberley D G., J. Heterocycl. Chem. 1980 17 1757
31. Fairley T A., Tidwell R R., Donkor I, Naiman N A., Ohemeng K A., Lombardy R J., Bentley J A., Cory M, J. Med. Chem. 1993 36 1746
32. Fujiok a H, Murai K, Ohba Y, Hiramatsu A, Kita Y, Tetrahedron Lett. 2005 46 2197
33. Peddibhotla S, Tepe J J., Synthesis 2003 1433
34. Huh D H., Ryu H, Kim Y G., Tetrahedron 2004 60 9857
35. Mitchell J M., Finney N S., Tetrahedron Lett. 2000 41 8431
36. You [nl]S L., Kelly J W., Org. Lett. 2004 6 1681; and references cited there
37. Alizadeh A, Babaki M, Zohreh N, Rezvanian A, Synthesis 2008 3793
38. Alizadeh A, Hosseinpour R, Rostamnia S, Synthesis 2008 3742
39. Alizadeh A, Zohreh N, Zhu L G., Tetrahedron 2009 65 2684
40. King F D., Tetrahedron 2007 63 2053
41. Allin S M., James S L., Martin W P., Smith T A. D., Tetrahedron Lett. 2001 42 3943