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Paper | Regular issue | Vol 31, No. 3, 1990, pp.505-516
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5249
■ A Facile One-Step Synthesis of Novel Polysubstituted Pyridines via the Tandem-Addition Rearrangement Hetaryne Reaction

Subhash P. Khanapure and Edward R. Biehl*

*Department of Chemistry, Southern Methodist University, P.O. Box 750314, Dallas, TX 75275-0314, U.S.A.

Abstract

Polysubstituted pyridines have been prepared in fair yields by a one-step reactionn of heteroarene 3-bromo-2,3-dimethoxy-5-(methoxymethyl)pyridine 3 and lithio alkyl- and lithio aryl-acetonitriles via the heteroaryne 13 generated from 3 by LDA in THF. Most lithio arylacetonitriles 4a-f yield rearranged products 5a-f by the tandem-addition rearrangement pathway and a 2:1 to 3:1 mixture of normal hetaryne products 6a-f and 7a-f. The other nitriles 4g-l give mixtures of the usual hetaryne products in ratios of 3:1 to 4:1, 6g-l:7g-l, respectively.