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Facile Synthesis of Dihydroquinoline‐Fused Canthines by Intramolecular Aza‐Diels–Alder Reaction
Author(s) -
Hutait Samiran,
Singh Virender,
Batra Sanjay
Publication year - 2010
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.201000925
Subject(s) - intramolecular force , chemistry , aldehyde , diels–alder reaction , lewis acids and bases , catalysis , intramolecular reaction , derivative (finance) , medicinal chemistry , stereochemistry , organic chemistry , financial economics , economics
The synthesis of dihydroquinoline‐fused canthines by intramolecular aza‐Diels–Alder reaction between N ‐prenylated 1‐formyl‐9 H ‐β‐carbolines and substituted anilines in the presence of a Lewis acid, followed by oxidation, is described. Additionally, it has been found that the N ‐protected aldehyde in the presence of a suitable catalyst [ZnBr 2 or Yb(OTf) 3 ] undergoes intramolecular carbonyl–ene reaction in a diastereoselective fashion to afford the syn or anti isomer of a new canthine derivative.
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