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Synthesis of 2‐acyl‐3‐methylthiofurans from 3‐methylthio‐2‐pentene‐1,5‐dione enolates
Author(s) -
Tinggaard M.,
Hansen P.,
Mogensen P. K.,
Simonsen O.,
Becher J.
Publication year - 1989
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.5570260233
Subject(s) - chemistry , pentene , nitro , sulfur , medicinal chemistry , iodine , oxygen , oxygen atom , organic chemistry , stereochemistry , catalysis , molecule , alkyl
2‐Acyl‐3‐methylthiofurans 3 are obtained in fair yields from 3‐methylthio‐2‐pentene‐1,5‐dione enolates 1 by reaction with iodine. In a similar reaction 1‐phenyl‐3‐methylthio‐4‐nitro‐2‐buten‐1‐one gave 3‐methylthio‐2‐nitro‐5‐phenylfuran 11. In the crystalline state the 2‐benzoyl‐3‐methylthio‐5‐phenylfuran 3b showed a non‐bonded sulfur‐oxygen interaction as inferred from an X‐ray diffraction determination, with a S····O distance of 2.871(5)Å.