Journal of heterocyclic chemistry

Acetylenic amides. 2. The generation and reactions of dianions derived from 2??propynamides

GM Coppola, RE Damon

Index: Coppola, Gary M.; Damon, Robert E. Journal of Heterocyclic Chemistry, 1995 , vol. 32, # 4 p. 1133 - 1140

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Citation Number: 13

Abstract

Abstract The dianion of N-benzyl-2-propynamide can be generated by the treatment of 4 with two equivalents of LDA at− 65 or ethylmagnesium bromide at− 20. The trilithio species 6 is readily formed using 3 equivalents of LDA. Reaction of 5 with aldehydes or ketones produce hydroxypropynamides 9 in good yields. Silation of 5a with chlorotrimethylsilane produces N-benzyl-3-trimethylsilyl-2-propynamide (13) in high yield. Reduction of 9 ...