Cycloadditions of 1,2,3-Triazines Bearing C5-Electron Donating Substituents: Robust Pyrimidine Synthesis

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• 作者：Christopher M. Glinkerman ; Dale L. Boger
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：August 21, 2015
• 年：2015
• 卷：17
• 期：16
• 页码：4002-4005
• 全文大小：337K
• ISSN：1523-7052

文摘

The examination of the cycloaddition reactions of 1,2,3-triazines 17鈥?b>19, bearing electron-donating substituents at C5, are described. Despite the noncomplementary 1,2,3-triazine C5 substituents, amidines were found to undergo a powerful cycloaddition to provide 2,5-disubstituted pyrimidines in excellent yields (42鈥?9%; EDG = SMe > OMe > NHAc). Even select ynamines and enamines were capable of cycloadditions with 17, but not 18 or 19, to provide trisubstituted pyridines in modest yields (37鈥?0% and 33% respectively).