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

• Published in: Bioorganic & 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
• Language: English
• 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

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.