Synthesis 2015; 47(02): 249-255
DOI: 10.1055/s-0034-1379112
paper
© Georg Thieme Verlag Stuttgart · New York

Formal Acylamination of Nitroalkenes in Aqueous Medium for the Synthesis of 2-Aryl-3-nitro-2,3-dihydroquinolin-4(1H)-ones

Atul Kumar Chaturvedi
a   Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, B.S. 10/1, Sector 10, Jankipuram extension, Sitapur Road, Lucknow 226031, India   Fax: +91(522)2771941   eMail: namrataiit@gmail.com   eMail: namrata.rastogi@cdri.res.in
b   Academy of Scientific and Innovative Research, New Delhi 110001, India
,
Namrata Rastogi*
a   Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, B.S. 10/1, Sector 10, Jankipuram extension, Sitapur Road, Lucknow 226031, India   Fax: +91(522)2771941   eMail: namrataiit@gmail.com   eMail: namrata.rastogi@cdri.res.in
b   Academy of Scientific and Innovative Research, New Delhi 110001, India
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Publikationsverlauf

Received: 26. Mai 2014

Accepted after revision: 20. August 2014

Publikationsdatum:
24. Oktober 2014 (online)


Abstract

Formal acylamination of aromatic nitroalkenes with N-(2-aminobenzoyl)benzotriazoles in aqueous methanol results in the diastereoselective synthesis of 2-aryl-3-nitro-2,3-dihydroquinolin-4(1H)-ones. The aliphatic nitroalkenes, however, form the Michael addition product with benzotriazole.

Supporting Information