Preparation of New Nitrogen-Bridged Heterocycles. 42. Synthesis and the Reaction of Pyridinium N-Ylides Using Bifunctional Ethyl Thiocyanatoacetates.

A Kakehi, S Ito, Y Hashimoto

Index: Kakehi, Akikazu; Ito, Suketaka; Hashimoto, Yasunobu Bulletin of the Chemical Society of Japan, 1996 , vol. 69, # 6 p. 1769 - 1776

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Citation Number: 14

Abstract

Various pyridinium (monosubstituted methylide) s were smoothly attacked to the cyano group in ethyl thiocyanatoacetate or ethyl 2-thiocyanatopropionate to afford the corresponding pyridinium (substituted cyanomethylide) s in low-to-moderate yields, while pyridinium (unsubstituted amidate) s reacted with the ester carbonyl group in the same reagents to give pyridinium (thiocyanatoaceto)-or (2-thiocyanatopropiono) amidates in ...