Microwave mediated facile one-pot synthesis of polyarylpyrroles from but-2-ene- and but-2-yne-1,4-diones

Tetrahedron

Volumn 60, Issue 7, 2004, Pages 1625-1630

  Rao, H Surya Prakash ^a   Jothilingam, S ^a   Scheeren, Hans W ^b  

^a PONDICHERRY UNIVERSITY   (India)

^b RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

Alkyl and aryl ammonium formates; Amination cyclization; Microwave assisted organic synthesis; Pyrrole synthesis; Reduction

Indexed keywords

ALKENE DERIVATIVE; ALKYNE DERIVATIVE; AMMONIUM DERIVATIVE; CARBON; KETONE DERIVATIVE; MACROGOL 200; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRROLE DERIVATIVE;

AMINATION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; HYDROGENATION; MICROWAVE IRRADIATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0742306820     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.11.087     Document Type: Article

References (32)

1. Jones R.A., Bean G.P. The chemistry of pyrroles. 1977;Academic, London. pp 1-5.
2. Sundberg R.J. Katritzky A.R., Rees C.W. Comprehensive heterocyclic chemistry. Vol. 4:1984;370 Pergamon, Oxford.
3. Sundberg R.J. Katritzky A.R., Rees C.W. Comprehensive heterocyclic chemistry II. Vol. 2:1996;149 Pergamon, Oxford.
4. Boger D.L., Boyce C.W., Labrili M.A., Sehon C.A., Jin Q. J. Am. Chem. Soc. 121:1999;54. and references cited therein.
5. Jones R.A. The chemistry of heterocyclic compounds. 1990;Wiley, Toronto. part 1 and 2.
6. Tietze L.F., Nordmann G. Synlett. 2001;337.
7. Groenendaal L., Meijer E.-W., Vekemans J.A.J.M. Müllen K., Wegner G. Electronic materials: the oligomer approach. 1997;Wiley-VCH, Weinheim.
8. Sakon, Y.; Ohnuma, T.; Hashimoto, M.; Saito, S.; Tsutsui, T.; Adachi, C. US Patent 5,077,142 A 19,911,231; 1991 CA 117:16862.
9. Paal C. Chem. Ber. 17:1884;2756.
10. Knorr L. Chem. Ber. 17:1884;2863.
11. Conant J.B., Lutz R.E. J. Am. Chem. Soc. 45:1923;1303.
12. Conant J.B., Lutz R.E. J. Am. Chem. Soc. 47:1925;881.
13. Coampaigne E., Foye W.O. J. Org. Chem. 17:1952;1405.
14. Demirdji S.H., Haddadin M.J., Issidorides C.H. J. Heterocycl. Chem. 22:1985;495.
15. Wilson R.M., Hengge A.C., Ataei A., Ho D.M. J. Am. Chem. Soc. 113:1991;7240.
16. Zhang J.-J., Schuster G.B. J. Am. Chem. Soc. 111:1989;7149.
17. Ram S., Ehrenkaufer R.E. Synthesis. 1988;91.
18. Rao H.S.P., Reddy K.S. Tetrahedron Lett. 35:1994;171.
19. Rao H.S.P., Jothilingam S. Tetrahedron Lett. 42:2001;6595.
20. Amarnath V., Anthony D.C., Amarnath K., Valentine W.M., Wetterau L.A., Graham D.G. J. Org. Chem. 56:1991;6924.
21. Patterson J.N., Soedigdo S. J. Org. Chem. 33:1968;2057.
22. Tsuge O., Tashiro M., Hokama K., Yamada K. Kogyo Kagaku Zasshi. 71:1968;1667. CA 70:37587.
23. Alper H., Prickett J.E. Inorg. Chem. 16:1977;67.
24. Schulte K.E., Reisch J., Walker H. Chem. Ber. 98:1965;98.
25. Alickmann D., Frohlich R., Maulitz A.H., Wurthwein E. Eur. J. Org. Chem. 2002;1523.
26. Periasamy M., Srinivas G., Bharathi P. J. Org. Chem. 64:1999;4204.
27. Chiu P.K., Samme M.P. Tetrahedron. 44:1988;3531.
28. Furstner A., Weintritt H., Hupperts A. J. Org. Chem. 60:1995;6637.
29. Lee C., Yang L., Hwu T., Feng A., Tseng J., Luh T. J. Am. Chem. Soc. 122:2000;4992.
30. Sera A., Fukumoto S., Yoneda T., Yamada H. Heterocycles. 24:1986;697.
31. Hong P., Yamazaki H. J. Organomet. Chem. 373:1989;133.
32. Kuhnert N. Angew Chem. Int. Ed. 41:2002;1863.