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Sc(OTf) 3 ‐Catalyzed Bicyclization of o ‐Alkynylanilines with Aldehydes: Ring‐Fused 1,2‐Dihydroquinolines
Author(s) -
Zhu Can,
Ma Shengming
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201406959
Subject(s) - reactivity (psychology) , ring (chemistry) , chemistry , amine gas treating , catalysis , indole test , medicinal chemistry , combinatorial chemistry , organic chemistry , medicine , alternative medicine , pathology
A Sc(OTf) 3 ‐catalyzed cascade Prins‐type cyclization reaction of o‐alkynylanilines, bearing a hydroxy or amine functionality, with aldehydes affords 1,2‐dihydroquinoline derivatives having an extra fused ring efficiently under mild reaction conditions. It is interesting to observe the reversed reactivity in the highly selective formation of 1,2‐dihydroquinoline derivatives instead of the formation of the usually favored indole derivatives.