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A novel intramolecular condensation of N-(2-cyanomethyltryptophyl)pyridinium tosylates

✍ Scribed by Frank DiNinno Jr.; William L. Heckle Jr.; Don K. Rehse; R.Marshall Wilson

Book ID: 104236815
Publisher: Elsevier Science
Year: 1972
Tongue: French
Weight: 235 KB
Volume: 13
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)84895-4

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✦ Synopsis

Condensations between pyridinium salts and enolate anions are of particular synthetic interest, since they constitute a useful means of constructing carbon-carbon bonds and yield dihydropyridines2 which might provide unusual intermediates for further elaboration into alkaloid systems. There are several examples of intermolecular condensations between enolates and pyridinium salts,3as well as a related intramolecular condensation that proceeds in good yield under extremely mild conditions (aqueous NaHC03).4 In the present work attention has been directed towards the cyclization of N-(2-cyanomethyltryptophyl)pyridinium salts, since salts of this type are known to exist as intramolecular charge-transfer (C-T) complexes,5 and therefore, might be expected to cyclize readily to any one of several possible dihydropyridines.

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