Base‐Induced Cyclization of Propargyl Alkenylsulfones: A High‐Yielding Synthesis of 4,5‐Disubstituted 2 H ‐Thiopyran 1,1‐Dioxides | Zendy

Hatial Ishita | Zendy; Das Joyee | Zendy; Ghosh Ananta K. | Zendy; Basak Amit | Zendy

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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.

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