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A Facile Approach to 3,4‐Oxepino‐Fused Tricyclic Indoles from MBH‐Acetates of Acetylenic Aldehydes via Successive Allylic Substitution/Intramolecular [3+2] Annulation †
Author(s) -
Reddy Chada Raji,
Sathish Puppala,
Valleti Reddi Rani
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201901496
Subject(s) - annulation , allylic rearrangement , intramolecular force , chemistry , yield (engineering) , medicinal chemistry , stereochemistry , substitution (logic) , catalysis , organic chemistry , materials science , computer science , metallurgy , programming language
Herein, we present our findings on the synthesis of 3,4‐oxepino‐fused indoles by a two‐step reaction sequence involving an initial allylic substitution followed by Rh(III)‐catalyzed intramolecular [3+2] annulation via C−H activation starting from Morita‐Baylis‐Hillman (MBH) acetates of acetylenic aldehydes. The strategy is amenable to broad range of MBH acetates providing a facile access to 3,4‐oxepino‐fused indoles in good yield.