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Synthesis of O,S‐Containing Polycycles via One‐Pot Michael Addition–Cycloacetalisation Cascade
Author(s) -
Bankar Siddheshwar K.,
Shirke Rajendra P.,
Ramasastry S. S. V.
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500505
Subject(s) - chemistry , michael reaction , cascade , lewis acids and bases , combinatorial chemistry , cascade reaction , organic chemistry , catalysis , chromatography
Abstract An efficient diversity‐oriented approach for the synthesis of previously unknown di‐, tri‐, tetra‐ and spirocyclic pyrano‐1,4‐dioxinones, pyrano‐1,4‐dithiinones and pyrano‐1,4‐oxathiinones from readily available starting compounds has been described. Cascade Michael addition–cycloacetalisation of acetoxy‐, alkoxy‐, and aryloxypyranones and 1,2‐dinucleophiles under mild Lewis acidic conditions provides a direct access to oxygen and sulfur‐containing complex heterocycles. Mechanistic aspects of the cascade process were elucidated in light of experimental facts. The methodology described herein shows high promise for the synthesis of several bioactive natural products as well as pharmaceutically important compounds.