Potassamide induced in situ benzylation of 5,6-dihydroisoquinolines: Structure of novel products

Kasturi, Tirumalai R and Arumugam, Subramaniam (1994) Potassamide induced in situ benzylation of 5,6-dihydroisoquinolines: Structure of novel products. In: Tetrahedron, 50 (46). 13277 -13284 .

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Abstract

Potassamide induced in situ benzylation of 1-alkyl-4-cyano-3-methoxy-5,6-dihydroisoquinolines (1a-b) with benzyl iodide gave the 5-benzyl-, 5,9-dibenzyl- and 4,4-dibenzyl-5,6-dihydroisoquinolines (9a-b, 8a-b and 10a-b), isoquinoline derivatives (4a-b) and diastereomeric mixture of 4-benzyl-1,2,3,4-tetrahydroisoquinolin-3(2H)-ones (11a-b & 11'a-b). Structures were assigned on the basis of spectral data [Mass, H-1 & C-13 NMR, 2D NOESY]. A few reactions carried out to transform the diastereomeric mixture of compounds 11a and 11's to the spirobenzylisoquinoline system 7a isomeric with naturally occurring ochotensane system ga are discussed.

Item Type:	Journal Article
Publication:	Tetrahedron
Publisher:	Elsevier science
Additional Information:	Copyright of this article belongs to Elsevier science.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	13 Apr 2011 12:23
Last Modified:	13 Apr 2011 12:23
URI:	http://eprints.iisc.ac.in/id/eprint/36697

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