Novel synthesis of 3, 5-disubstituted pyridines by 1, 4-cycloaddition of 1-aza-1, 3-butadienes with enamines

…, S Takamatsu, M Uesaka, S Yamamoto…

Index: Komatsu, Mitsuo; Takamatsu, Shigeki; Uesaka, Masatoshi; Yamamoto, Shinji; Ohshiro, Yoshiki; Agawa, Toshio Journal of Organic Chemistry, 1984 , vol. 49, # 15 p. 2691 - 2699

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Citation Number: 27

Abstract

A new method for the synthesis of 3, 5-disubstituted pyridines is described. Reactions of the N-substituted methanimines 1 with the 8-substituted enamines 2 give l-aza-1, 3-butadienes 3a-i and/or symmetrically 3, 5-disubstituted pyridines 4a-c, eh in moderate to good yields. At reaction temperatures of 150" C the azadienes 3 are the predominant products, and the reaction provides a good route to 1-azadienes with no substituent at the 4-position. At ...