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Reaction of 4-cyano-1,3-dihydroxy-5,6,7,8-tetrahydroisoquinolines with Vilsmeier Reagent: Structure and Mechanism of Formation of [2,7]naphthyridines

Kasturi, Tirumalai R and Arumugam, Subramaniam and Mathew, Lata and Jayaram, Srirangam K and Dastidar, Parthasarathi and Guru Row, Tayur N (1992) Reaction of 4-cyano-1,3-dihydroxy-5,6,7,8-tetrahydroisoquinolines with Vilsmeier Reagent: Structure and Mechanism of Formation of [2,7]naphthyridines. In: Tetrahedron, 48 (31). pp. 6499-6510.

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Abstract

Reaction of 4-cyano-1,3-dihydroxy-5,6-7,8-tetrahydroisoquinoline 1, with Vilsmeier reagent gave the chloro aldehyde 2, dichloro [2,7]naphthyridine, 5 and monochloro [2,7]naphthyridine 8, identified by spectral data [Mass, $^1H$ & $^{13}C$ NMR, NOE and HETERO COSY]. Structure 5 has been confirmed by X-ray crystal structure analysis. Reaction of 1a-f, similarly, gave the corresponding compounds 2a-f, 5a-f and 8a-f. The starting tetrahydroisoquinolines, 1a-f were synthesised by the reaction of the corresponding $\beta$-keto esters with cyanoacetamide. Reaction of 8 with $POCl_3$ gave in almost quantitative yield, the dichloro compound 5. An acceptable mechanism has been proposed for the formation of the products.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier Science Ltd.
Keywords: tetrahydroisoquinolines;Vilsmeier reagent;naphthyridines
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 06 Dec 2007
Last Modified: 19 Sep 2010 04:41
URI: http://eprints.iisc.ernet.in/id/eprint/12752

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