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Solvent‐Controlled Bifurcated Cascade Process for the Selective Preparation of Dihydrocarbazoles or Dihydropyridoindoles
Author(s) -
Mo DongLiang,
Wink Donald J.,
Anderson Laura L.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403268
Subject(s) - cascade , process (computing) , chemistry , solvent , combinatorial chemistry , chromatography , computer science , organic chemistry , operating system
A solvent‐controlled cascade process has been identified for the dual purpose of the preparation of either dihydrocarbazoles or dihydropyridoindoles from identical N‐aryl‐α,β‐unsaturated nitrones and electron‐deficient allene starting materials. These reactions proceed smoothly under mild metal‐free conditions affording a range of two types of skeletally distinct indole‐based heterocycles in high yield and diastereoselectivity. These transformations demonstrate the use of a bifurcated cascade process that hinges on the ring‐opening event of a benzazepine intermediate for the synthesis of skeletally diverse heterocyclic products and rapid access to biologically‐significant, indole‐based structures.