One-carbon compounds as synthetic intermediates. The synthesis of hydropyrimidines and hydroquinazolines by sequential nucleophilic addition to diphenyl …

…, CJ Hobbs, R Wrigglesworth

Index: Garratt, Peter J.; Hobbs, Christopher J.; Wrigglesworth, Roger Journal of Organic Chemistry, 1989 , vol. 54, # 5 p. 1062 - 1069

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Citation Number: 35

Abstract

Diphenyl cyanocarbonimidate (1) undergoes nucleophilic addition with w-amino esters and amines in a sequential manner to give guanidine derivatives that, for the most part, spontaneously cyclize to give hydropyrimidines or hydroquinazolines. The hydropyrimidines could be dehydrogenated to dihydropyrimidines, and the NCN group could be hydrolyzed to a carbonyl or amine group in the pyrimidine and to an. amine group in the quinazoline ...