1, 3-Dipolar cycloaddition reactions of diazopyrazolinones with electron-deficient dipolarophiles

A Padwa, AD Woolhouse, JJ Blount

Index: Padwa, Albert; Woolhouse, Anthony D.; Blount, John J. Journal of Organic Chemistry, 1983 , vol. 48, # 7 p. 1069 - 1074

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Citation Number: 19

Abstract

A study of the reactivity of a series of 4-diazopyrazolin-5-ones toward dipolar cycloaddition with electron-deficient olefinic and acetylenic dipolarophiles has been carried out. Reactions with dimethyl acetylenedicarboxylate afford pyrazolo [1, 5-d][1, 2, 4] triazin-7-ones which result from dipolar cycloaddition followed by a van Alphen-Huttel rearrangement of the initially produced spiro 3H-pyrazole adducts. Reaction with unsymmetrical acetylenic ...