A K2CO3-Mediated Regioselective Synthesis of Indole/Pyrrole-Fused 1,4-Oxazines: An Unexpected Indole-Fused Azlactone Synthesis

作者:Vandavasi Jaya Kishore; Hu Wan Ping; Senadi Gopal Chandru; Boominathan Siva Senthil Kumar; Chen Hsing Yin*; Wang Jeh Jeng
来源:European Journal of Organic Chemistry, 2014, 2014(28): 6219-6226.
DOI:10.1002/ejoc.201402818

摘要

A highly regioselective and efficient base-catalyzed intramolecular hydroalkoxylation of primary and secondary alkynyl alcohols was developed to afford 1,4-oxaza heterocycles. Although the rates of cyclization for terminal alkynyl alcohols were significantly greater than those for internal ones, our method tolerated both terminal and internal alkynes. In addition, an unprecedented one-pot hydroamination reaction was found to proceed with high chemo- and regioselectivity to form indole-fused azlactones in the presence of base.

  • 出版日期2014-10