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Synthesis and reaction of 6‐substituted 3‐methoxycarbonyl‐4‐methylthio‐2 H ‐pyran‐2‐one derivatives
Author(s) -
Tominaga Yoshinori,
Ushirogochi Atsuyuki,
Matsuda Yoshiro
Publication year - 1987
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570240612
Subject(s) - chemistry , pyran , sodium methoxide , nucleophile , aryl , potassium hydroxide , methanol , methoxide , reagent , medicinal chemistry , hydrogen peroxide , dimethyl sulfoxide , sodium hydroxide , sulfoxide , organic chemistry , catalysis , alkyl
Reaction of aryl and styryl methyl ketones 1a‐m with dimethyl bis(methylthio)methylenemalonate ( 2 ) in the presence of potassium hydroxide in dimethyl sulfoxide gave the corresponding methyl 6‐aryl‐ and 6‐styryl‐4‐methylthio‐2‐oxo‐2 H ‐pyran‐3‐carboxylates 3a‐m . 6‐Aryl derivatives 3a‐d,g were treated with sodium methoxide in methanol to give the corresponding 6‐aryl‐4‐methoxy‐2 H ‐pyran‐2‐ones 8a‐d and 9. Phenylcoumalin ( 7a ) and paracotoin ( 7b ) were synthesized by the desulfurization of 6‐aryl‐4‐methylthio‐2 H ‐pyran‐2‐ones 4a,b. Similarly, anibine ( 8e ) was also synthesized from 3g . Treatment of 3 with hydrogen peroxide or 3‐chloroperoxybenzoic acid gave the corresponding 4‐methylsulfiny‐2 H ‐pyran‐2‐ones 10a‐f in good yields. Displacement reactions of 10a‐f with nucleophilic reagents are also described.