Selective synthesis of some 4,5-dihydro-2H-benzo[g]indazoles and 8,9-dihydro-2H-benzo[e]indazoles via the Vilsmeier-Haack reaction under thermal and microwave assisted conditions

Journal of Heterocyclic Chemistry

Volumn 43, Issue 2, 2006, Pages 389-394

  Sivaprasad, Ganesabaskaran ^a   Sridhar, Radhakrishnan ^a   Perumal, Paramasivan T ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2,4 DINITROPHENYL) 4,5 DIHYDRO 2H BENZO[G]INDAZOLE; 2 (2,4 DINITROPHENYL) 6 METHOXY 4,5 DIHYDRO 2H BENZO[G]INDAZOLE; 2 (2,4 DINITROPHENYL) 7 METHOXY 4,5 DIHYDRO 2H BENZO[G]INDAZOLE; 2 (2,4 DINITROPHENYL) 8 METHOXY 4,5 DIHYDRO 2H BENZO[G]INDAZOLE; 2 (2,4 DINITROPHENYL) 8,9 DIHYDRO 2H BENZO[E]INDAZOLE; 2 (4 NITROPHENYL) 4,5 DIHYDRO 2H BENZO[G]INDAZOLE; 2 (4 NITROPHENYL) 8,9 DIHYDRO 2H BENZO[E]INDAZOLE; 2 PHENYL 4,5 DIHYDRO 2H BENZO[G]INDAZOLE; 4,5 DIHYDRO 2H BENZO[G]INDAZOLE; 4,5 DIHYDRO 2H BENZO[G]INDAZOLE DERIVATIVE; 6 METHOXY 2 (4 NITROPHENYL) 4,5 DIHYDRO 2H BENZO[G]INDAZOLE; 7 METHOXY 2 (4 NITROPHENYL) 4,5 DIHYDRO 2H BENZO[G]INDAZOLE; 7 METHOXY 4,5 DIHYDRO 2H BENZO[G]INDAZOLE; 8 METHOXY 2 (4 NITROPHENYL) 4,5 DIHYDRO 2H BENZO[G]INDAZOLE; 8 METHOXY 2 PHENYL 4,5 DIHYDRO 2H BENZO[G]INDAZOLE; 8,9 DIHYDRO 2H BENZO[E]INDAZOLE DERIVATIVE; HYDRAZONE DERIVATIVE; INDAZOLE DERIVATIVE; TETRALIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG SYNTHESIS; MICROWAVE RADIATION; PHARMACOPHORE; VILSMEIER HAACK REACTION;

EID: 33645229091     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570430219     Document Type: Article

References (30)

1. S. Caron and E. Vazquez, Synthesis, 4, 588 (1999).
2. S. Schenone, O. Bruno, A. Ranise, C. Brullo, F. Bondavalli, W. Filippelli, F. Mazzeo, A. Capuano and G. Falcone, Il Farmaco, 58, 845 (2003).
3. O. Kayser, W. R. Waters, K. M. Woods, S. J. Upton, J. S. Keithly, H. Laatsch and A. F. Kiderlen J. Antimicrobial Chemotherapy, 50, 975 (2002).
4. A. S. Kalgutkar and Z. Zhao, Current Drug Targets, 28, 79, (2001).
5. I. Collins, M. Rowley, W. B. Davey, F. Emms, R. Marwood, S. Patel, A. Fletcher, I. C. Ragan, P. D. Leeson, A. L. Scott and T. Broten. Bioorg. Med. Chem., 9, 1655 (1998).
6. G. A. Pinna, M. A. Pirisi, J. M. Mussinu, G. Loriga, A. Pau and G. E. Grella, Il Farmaco, 58, 749, (2003).
7. B. J. Douglas, S. B. Gregory, Der-Ing Liao, M. P. J. Wynona, N. W. Kevin and A. W. David J. Mol. Graphics Modell., 19, 435 (2001).
8. I. Collins, M. Rowley, W. B. Davey, F. Emms, R. Marwood, S. Patel, S. Patel, A. Fletcher, I. C. Ragan, P. D. Leeson, A. L. Scott and T. Broten, Biorg. Med. Chem. 6, 743 (1998).
9. For Reviews on the Vilsmeier-Haack Reaction, [a] C. M. Marson, Tetrahedron 48, 3659 (1992);
10. [b] S. Seshadri, J. Sci. Ind. Res. 32, 128 (1973);
11. [c] O. Meth-Cohn and S. P. Stanforth, Comprehensive Organic Synthesis, eds B. M. Trost and I. Fleming, Vol. ed. C. H. Heathcock, Pergamon, Oxford, 2, 777 (1991).
12. C. Jutz, Advances in Organic Chemistry, ed. E. C. Taylor, John Wiley & Sons, New York, 9, 225 (1976).
13. G. Jones and S. P. Stanforth, Org. React., 49, 1 (1997).
14. S. Seshadri, J. Sci. Ind. Res., 32, 128 (1973).
15. C. M. Marson. Tetrahedron, 48, 3659 (1992).
16. O. Meth-Cohn and S. P. Stanforth, Comprehensive Organic Synthesis, eds B. M. Trost and I. Fleming, Vol. ed. C. H. Heathcock, Pergamon, Oxford, 2, 777 (1991).
17. [15a] V. J. Majo and P. T. Perumal, Tetrahedron Lett. 37, 5015 (1996);
18. [b] V. J. Majo and P. T. Perumal, J. Org. Chem. 61, 6525 (1996);
19. [c] R. R. Amaresh and P. T. Perumal, Tetrahedron Lett., 38, 7287 (1997);
20. [d] S. Selvi and P. T. Perumal, Tetrahedron Lett., 38, 6263 (1997);
21. [e] V. J. Majo and P. T. Perumal, J. Org. Chem., 63, 7136 (1998).
22. R. Rajagopal and S. Seshadri, Dyes and Pigments, 17, 57 (1991).
23. [17a] O. Meth-Cohn and B. Tarnowski, Adv. Heterocycl. Chem., 31, 207 (1982);
24. [b] O. Meth-Cohn, Heterocycles, 35, 539 (1993).
25. M. A. Kira, M. D. Abdel-Rehman and K. Z. Gadella, Tetrahedron Lett., 109, (1969).
26. S. Selvi and P. T. Perumal, Indian J. Chem., 39B, 163 (2000).
27. R. Sridhar, G. Sivaprasad and P. T. Perumal, J. Heterocyclic Chem., 41, 405 (2004).
28. M. A. Kira, M. N. Aboul-Enein and M. I. Korkor, J. Heterocyclic Chem., 7, 25 (1970).
29. M. Weissenfels, H. Schurig, and G. Huchsam, Z. Chem., 6. 471 (1966).
30. K. J. Ray, S. Sharma and G. B. Chatterjee, Synth. Commun., 9, 727 (1979).