Synthesis of 2‐acyl‐3‐methylthiofurans from 3‐methylthio‐2‐pentene‐1,5‐dione enolates | Zendy

Tinggaard M. | Zendy; Hansen P. | Zendy; Mogensen P. K. | Zendy; Simonsen O. | Zendy; Becher J. | Zendy

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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.

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