Regioselective oxidation of 2-amino-3-aroyl-4,5-dialkylthiophenes by DMSO

Solutions of 2-amino-3-aroyl-4,5-dialkylthiophenes in DMSO (dimethyl sulfoxide) undergo regioselective oxidation of benzylic carbon under mild conditions. We describe three examples and propose a mechanism for oxidation.

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Bibliographic Details
Published inBioorganic & medicinal chemistry letters Vol. 14; no. 4; pp. 929 - 933
Main Authors JOSHI, Elizabeth, CHORDIA, Mahendra D, MACDONALD, Timothy L, LINDEN, Joel, OLSSON, Ray
Format Journal Article
LanguageEnglish
Published Oxford Elsevier 23.02.2004
Subjects
Biological and medical sciences
Chemistry
Dimethyl Sulfoxide - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Medical sciences
Miscellaneous
Molecular Structure
Organic chemistry
Oxidation-Reduction
Pharmacology. Drug treatments
Preparations and properties
Thiophenes - chemistry
Thiophene derivatives
Agonist
Sulfur heterocycle
Methyl sulfoxide
Regioselectivity
Reaction mechanism
A1 Adenosine receptor
Oxidation
Ketone
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Summary:Solutions of 2-amino-3-aroyl-4,5-dialkylthiophenes in DMSO (dimethyl sulfoxide) undergo regioselective oxidation of benzylic carbon under mild conditions. We describe three examples and propose a mechanism for oxidation.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2003.12.010