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Base‐Induced Cyclization of Propargyl Alkenylsulfones: A High‐Yielding Synthesis of 4,5‐Disubstituted 2 H ‐Thiopyran 1,1‐Dioxides
Author(s) -
Hatial Ishita,
Das Joyee,
Ghosh Ananta K.,
Basak Amit
Publication year - 2015
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.201500633
Subject(s) - thiopyran , chemistry , propargyl , aryl , base (topology) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , mathematical analysis , alkyl , mathematics
A convenient synthesis of 4,5‐disubstituted 2 H ‐thiopyran 1,1‐dioxides is reported through a base induced process starting from eneyne sulfones. Except for strongly electron‐withdrawing groups, the reaction tolerated a wide variety of substituents in the two aryl rings. This finding represents a major departure from the behaviour of the corresponding ethers. The reaction most probably proceeds through a 6π‐electrocyclization from an in‐situ‐generated 1,3,5‐trienyl sulfinate.