Facile synthesis of 3(α,β-diaryl vinyl)indoles under conventional and solvent-free microwave irradiation

Synthetic Communications

Volumn 35, Issue 7, 2005, Pages 923-927

  Jaisankar, Pichamuthu ^a   Srinivasan, Panayencheri C ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

2 methyl 3 diarylvinylindoles; Conventional and microwave conditions; Montmorillonite K10 clay; Phosphoryl chloride

Indexed keywords

3 VINYLINDOLE DERIVATIVE; CHLORIDE; INDOLE DERIVATIVE; MONTMORILLONITE; SOLVENT; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CLAY; MELTING POINT; MICROWAVE RADIATION; REACTION ANALYSIS; SOLID; SYNTHESIS; X RAY DIFFRACTION;

EID: 16444376430     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200051689     Document Type: Article

References (15)

1. (a) Jiang, B.; Yang, C. G.; Wang, J. Enantioselective synthesis for the (-)-antipode of the pyrazinone marine alkaloid, hama canthin A. J. Org. Chem. 2001, 66, 4865;
2. (b) Rajeswaran, W. G.; Labroo, R. B.; Cohen, L. A.; King, M. Sythesis of 5-[(indol-2-one-3-yl) methyl]-2, 2-dimethyl-1, 3-dioxane-4, 6-diones, and spiro cyclo propyloxyindole derivatives. J. Org. Chem. 1999, 64, 1369.
3. Sundberg, R. J. Indoles; Academic Press: New York, 1996; pp. 105-118; Chapter 11.
4. (a) Pindur, U.; Otto, C. A new access to 2′-amino-substituted vinyl indoles as donor-activated heterocyclic dienes and their first Diels-Alder reactions. Tetrahedron. 1992, 48, 3515.
5. Pfeuffer, L.; Pindur, U. New reaction of 3-vinyl and 3-(2-propenyl) indoles with N-phenyl maleimide; [4 + 2] cycloaddition-ene reaction and dimerization. Helv. Chim. Acta. 1988, 71, 467.
6. (a) Pindur, U.; Kim, M. H. New reaction of 2-vinylindoles with azodienophiles: Diels-Alder reaction versus Michael-type addition. Heterocycles 1988, 27, 967;
7. (b) Pindur, U.; Eitel, M. Reactions of 2-vinylindoles with carbodienophiles: Synthetic and mechanistic aspects. J. Org. Chem. 1990, 55, 5369.
8. (a) Pindur, U.; Kim, M. H.; Rogge, M.; Massa, W.; Molinier, M. Diels-Alder reactions of (1H-indol-3-yl)-enacetamides-and-endiacetamides; A selective access to acetylamino-functionalised[b] annelated indoles and carbazoles. Helv. Chim. Acta. 1991, 74, 727.
9. Medio-Soon, M.; Otto, C.; Pindur, U. Reactions of 3-(Tetrahydropyrid-4- yl)-indoles with dienophiles: new heterocyclic functionalized indoles and pyrido[c] annellated carbazoles. Tetrahedron Lett. 1991, 32, 1771.
10. Medio-Soon, M.; Pindur, U. New reactions of amino-functionalized 3-vinyl-1H-indoles and tetra hydro pyridine-4-yl analogues with dienophiles. Helv. Chim. Acta. 1991, 74, 430.
11. Wilkens, J.; Kühling, A.; Blechert, S. Nuclephilic additions to acceptors-substituted 2-vinyl indoles. Tetrahedron 1987, 43, 3237.
12. Kansal, V. K.; Potier, P. The biogenetic, synthetic and bio-chemical aspects of ellipticine and antitumour alkaloids. Tetrahedron 1986, 42, 2389.
13. Kannadasan, S.; Srinivasan, P. C. A facile synthesis of 2-[4′-dimethylaminophenyl]-3-aryl-β-carbolinium phenyl sulfonates. Tetrahedron Lett. 2002, 43, 3149.
14. Mohanakrishnan, A. K.; Srinivasan, P. C. A versatile construction of the 8H-Quino [4,3-b]carbazole ring system as a potential DNA binder. J. Org. Chem. 1995, 60, 1939.
15. Noland, W. E.; Robinson, D. N. Synthesis of 3-vinylindoles. J. Org. Chem. 1957, 1134.