α-Oxoketene dithioacetals mediated heteroaromatic annulation protocol for benzoheterocycles: An efficient regiocontrolled synthesis of highly substituted and annulated indazoles

Tetrahedron

Volumn 60, Issue 15, 2004, Pages 3457-3464

  Peruncheralathan, S ^a   Khan, T A ^a   Ila, H ^a   Junjappa, H ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^b BioOrganics & Applied Materials Pvt Ltd   (India)

Author keywords

Oxoketene dithioacetals; Benzoheterocycles; Heteroaromatic annulation; Indazoles

Indexed keywords

1,3 DIPHENYL 3,6 DIHYDROINDENO[1,2 E]INDAZOLE; 1,3 DIPHENYL 5 CYANOMETHYLPYRAZOLE; 1,3 DIPHENYL 5 METHYLTHIO 3,6 DIHYDROINDENO[1,2 E]INDAZOLE; 1,3 DIPHENYL 5 METHYLTHIO 6,7 DIHYDRO 3H NAPHTHO[1,2 E]INDAZOLE; 1,3 DIPHENYL 5 METHYLTHIO 6,7,8,9 TETRAHYDRO 3H BENZO[E]INDAZOLE; 1,3 DIPHENYL 6,7 DIHYDRO 3H NAPHTHO[1,2 E]INDAZOLE; 1,3 DIPHENYL 6,7,8,9 TETRAHDYRO 3H BENZO[E]INDAZOLE; 1,3,4 TRIS(PHENYL) 1H 7 INDAZOLE; 11 CYANO 1,3 DIPHENYL 4 METHYLTHIO 5,6,7,8,9,10 HEXAHYDRO 1H CYCLOOCTA[F]INDAZOLE; 3 (1,3 DIPHENYL 1H 5 PYRAZOLYL) 4 METHYLTHIO 2H PYRANO[3,2 C]QUINOLIN 2 ONE; 4 CYANO 1,3 DIPHENYL 5 METHYLTHIO 3,6 DIHYDROINDENO[1,2 E]INDAZOLE; 4 CYANO 1,3 DIPHENYL 5 METHYLTHIO 3,6,7,8 TETRAHYDROCYCLOPENT[E]INDAZOLE; 4 CYANO 1,3 DIPHENYL 5 METHYLTHIO 6,7 DIHYDRO 3H NAPHTHO[1,2 E]INDAZOLE; 4 CYANO 1,3 DIPHENYL 5 METHYLTHIO 6,7,8,9 TETRAHYDRO 3H BENZ[E]INDAZOLE; 6 METHYLTHIO 1,3,4 TRIS(PHENYL) 1H 7 INDAZOLE; 7 CYANO 1,3 DIPHENYL 4 FORMYL 6 METHYLTHIO 1H INDAZOLE; 7 CYANO 1,3 DIPHENYL 4 METHYL 6 METHYLTHIO 1H INDAZOLE; 7 CYANO 4,5 DIMETHYL 1,3 DIPHENYL 6 METHYLTHIO 1H INDAZOLE; 7 CYANO 6 METHYLTHIO 1,3,4 TRIS(PHENYL) 1H INDAZOLE; ACETAL DERIVATIVE; HETEROCYCLIC COMPOUND; INDAZOLE DERIVATIVE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ANNULATION REACTION; AROMATIZATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLOADDITION; DRUG CONJUGATION; DRUG SYNTHESIS; ELIMINATION REACTION; PRIORITY JOURNAL;

EID: 1642415685     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.02.029     Document Type: Article

References (41)

1. Caron S., Vazquez E. Synthesis. 4:1999;588. and references cited therein.
2. Yeu J.-P., Yeh J.-T., Chen T.-Y., Uang B.-J. Synthesis. 1775:2001;. and references cited therein.
3. Sun J.-H., Teleha C.A., Yan J.-S., Rodgers J.D., Nugiel D.A. J. Org. Chem. 62:1997;5627.
4. Rodgers J.D., Johnson B.L., Wang H., Greenberg R.A., Erickson-Viitanen S., Klabe R.M., Cordova B.C., Rayner M.M., Lam G.N., Chang C.-H. Biorg. Med. Chem. Lett. 6:1996;2919.
5. Norman M.H., Navas F. III, Thompson J.B., Rigdon G.C. J. Med. Chem. 39:1996;4692.
6. Yoshida T., Matsuura N., Yamamoto K., Doi M., Shimada K., Morie T., Kato S. Heterocycles. 43:1996;2701.
7. Robertson D.W., Bloomquist W., Cohen M.L., Reid L.R., Schenck K., Wong D.T. J. Med. Chem. 33:1990;3176.
8. Villalobos A., Blake J.F., Biggers C.K., Butler T.W., Chapin D.S., Chen Y.L., Ives J.L., Jones S.B., Liston D.R., Nagel A.A., Nason D.M., Nielsen J.A., Shalaby I.A., White W.F. J. Med. Chem. 37:1994;2721.
9. Mylari B.L., Zembrowski W.J., Beyer T.A., Aldinger C.E., Siegel T.W. J. Med. Chem. 35:1992;2155.
10. Elguero J. Pyrazole and their benzo derivatives. Katritzkey A.R., Rees C.W., Potts K.T. Comprehensive heterocyclic chemistry. Vol. 5:1984;167 Pergamon, New York.
11. Behr L.C., Fusco R., Jarobe C.H. Wiley R.H. Pyrazoles, pyrazolines, pyrazolidines, indazoles and condensed rings. 1969;289 Wiley Science, New York.
12. Sainsbury M. Caffey S., Ansell M.F. 2nd ed. Rodd's chemistry of carbon compounds. Vol. 4:1986;93 Elsevier, New York. part C.
13. Ruechardt C., Hassmann V. Liebigs Ann. Chem. 1980;908.
14. Dell'Erba C., Novi M., Petrillo G., Tavani C. Tetrahedron. 48:1992;325.
15. Kunka C.P.A., Warkentin J. Can. J. Chem. 68:1990;575.
16. Huisgen R., Bast K. Organic syntheses. Collect. vol. V. 1973;Wiley, New York. p 650.
17. Boudreault N., Leblanc Y. Org. Synth. 74:1996;241.
18. Reddy K.R., Roy A., Ila H., Junjappa H. Tetrahedron. 51:1995;10941.
19. Roy A., Reddy K.R., Ila H., Junjappa H. J. Chem. Soc., Perkin Trans. 1. 1999;3001.
20. Barluenga J., Aznar F., Palomero M.A. Chem. Eur. J. 7:2001;5318.
21. Mediò-Simon M., Alvarez de Laviada M.J., Sequlveda Arques J. J. Chem. Soc., Perkin Trans. 1. 1990;2749.
22. Review: (a) Ila H., Junjappa H., Mohanta P.K. Gribble G.W., Gilchrist T.L. Progress in heterocyclic chemistry. Vol. 13:2001;1 Pergamon, Oxford. Chapter 1.
23. Junjappa H., Ila H., Asokan C.V. Tetrahedron. 46:1990;5423.
24. Junjappa H., Ila H., Patro B., Rao C.S. J. Indian Chem. Soc. 71:1994;501.
25. Suresh J.R., Syam Kumar U.K., Ila H., Junjappa H. Tetrahedron. 57:2001;781.
26. Suresh J.R., Barun O., Ila H., Junjappa H. Tetrahedron. 56:2000;8153.
27. Barun O., Patra P.K., Ila H., Junjappa H. Tetrahedron Lett. 40:1999;3797.
28. Basveswara Rao M.V., Syam Kumar U.K., Ila H., Junjappa H. Tetrahedron. 55:1999;11563.
29. Kishore K., Reddy K.R., Suresh J.R., Ila H., Junjappa H. Tetrahedron. 55:1999;7645.
30. Patra P.K., Suresh J.R., Ila H., Junjappa H. Tetrahedron. 54:1998;10167.
31. Syam Kumar U.K., Patra P.K., Ila H., Junjappa H. Tetrahedron Lett. 39:1998;2029.
32. Suresh J.R., Patra P.K., Ila H., Junjappa H. Tetrahedron. 53:1997;14737.
33. Patra P.K., Suresh J.R., Ila H., Junjappa H. Tetrahedron Lett. 38:1997;3119.
34. Satyanarayana J., Reddy K.R., Ila H., Junjappa H. Tetrahedron Lett. 33:1992;6173.
35. Reddy K.R., Ila H., Junjappa H. Synthesis. 1995;929.
36. Balu M.P., Pooranchand D., Ila H., Junjappa H. Tetrahedron Lett. 29:1988;501.
37. Pooranchand D., Satyanarayana J., Ila H., Junjappa H. Synthesis. 1993;241.
38. Sangwan N.K., Kelkar P.M., Rastogi S.N., Anand N. Ind. J. Chem. 24B:1985;639.
39. Vogel A.I. Textbook of practical organic chemistry. 5th ed. 1989;ELBS, London. p 1149.
40. Kumar A., Malhotra S., Vats A., Himanshu, Singh S.K., Sharma S.K., Prasad A.K., Errington W., Olsen C.E., Jain S.C., Parmar V.S. Ind. J. Chem. 41B:2002;360.
41. Chauhan S.M.S., Junjappa H. Tetrahedron. 32:1976;1779.