Novel triethylamine mediated thermal reactions of 3-aryl-2-cyanoprop-2-enoic acid derivatives-demethylation, reduction and vinylogation

Harisha, Attimogae Shivamurthy and Nayak, Suresh Parameshwar and Nagarajan, Kuppuswamy and Row, Tayur Narasingarow Guru and Hosamani, Amar A (2015) Novel triethylamine mediated thermal reactions of 3-aryl-2-cyanoprop-2-enoic acid derivatives-demethylation, reduction and vinylogation. In: TETRAHEDRON LETTERS, 56 (11). pp. 1427-1431.

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Abstract

3-Aryl-2-propenoic acid derivatives undergo interesting reactions with hot triethylamine. Substrates like 6 having a methoxyl with a nitro in the ortho and cyanoacrylic derivatives in the para positions give O-demethylated products, for example, entacapone 7. On the other hand compounds like 16 having the NO2 in the para and cyanoacrylic in the ortho position undergo reduction and vinylogation. The latter phenomenon is observed in the absence of the NO2 group also. (C) 2015 Elsevier Ltd. All rights reserved.

Item Type:	Journal Article
Publication:	TETRAHEDRON LETTERS
Publisher:	PERGAMON-ELSEVIER SCIENCE LTD
Additional Information:	Copy right for this article belongs to the PERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Keywords:	3-Aryl-2-cyanoprop-2-enoates; Triethylamine; Demethylation; Entacapone; Reduction; Vinylogation
Department/Centre:	Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Date Deposited:	20 Apr 2015 11:05
Last Modified:	20 Apr 2015 11:05
URI:	http://eprints.iisc.ac.in/id/eprint/51285

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