The Journal of Organic Chemistry

Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Azadienes:[4+ 2] Cycloaddition Reaction of Amidines with 1, 3, 5-Triazines

DL Boger, MJ Kochanny

Index: Boger, Dale L.; Kochanny, Monica J. Journal of Organic Chemistry, 1994 , vol. 59, # 17 p. 4950 - 4955

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Citation Number: 43

Abstract

A detailed study of the scope of the amidine Diels-Alder reaction with 1, 3, 5-triazines is described. The thermal reaction of amidines with symmetrical 1, 3, 5-triazines proceeds with in situ amidine to 1, l-diaminoethene tautomerization,[4+ 21 cycloaddition with the 1, 3, 5- triazine, loss of ammonia from the initial Diels-Alder adduct with imine generation, imine to enamine tautomerization, and retro Diels-Alder loss of ethyl cyanoformate to provide ...