Thermal cycloaddition of 1, 3, 5-triazine with enamines: regiospecific pyrimidine annulation

DL Boger, J Schumacher, MD Mullican…

Index: Boger, Dale L.; Schumacher, Jane; Mullican, Michael D.; Patel, Mona; Panek, James S. Journal of Organic Chemistry, 1982 , vol. 47, # 13 p. 2673 - 2675

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Citation Number: 55

Abstract

A recent study of Neunhoeffer and Bachmann has demonstrated that 1, 3, 5-triazine (2) undergoes a rapid and regiospecific cycloaddition reaction with ynamines, and the subsequent loss of hydrogen cyanide provided a simple pyrimidine~ ynthesis.~ In addition, Neunhoeffer has shown that a symmetrical enamine, l-pyrrolidinocyclopentene, participates in a similar cycloaddition reaction with 2 and affords the pyrimidine product 3b after loss of ...