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A K 2 CO 3 ‐Mediated Regioselective Synthesis of Indole/Pyrrole‐Fused 1,4‐Oxazines: An Unexpected Indole‐Fused Azlactone Synthesis
Author(s) -
Vandavasi Jaya Kishore,
Hu WanPing,
Senadi Gopal Chandru,
Boominathan Siva Senthil Kumar,
Chen HsingYin,
Wang JehJeng
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402818
Subject(s) - regioselectivity , chemistry , indole test , hydroamination , pyrrole , intramolecular force , combinatorial chemistry , catalysis , base (topology) , stereochemistry , medicinal chemistry , organic chemistry , mathematical analysis , mathematics
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.