A novel acid-catalyzed rearrangement of 2-substituted-3-(2-nitrophenyl)oxiranes for the synthesis of di- and mono-oxalamides. Issue 33 (16th March 2016)

• Record Type: Journal Article
• Authors: Mamedov, Vakhid A.; Mamedova, Vera L.; Khikmatova, Gul'nas Z.; Mironova, Ekaterina V.; Krivolapov, Dmitry B.; Bazanova, Olga B.; Chachkov, Denis V.; Katsyuba, Sergey A.; Rizvanov, Il'dar Kh; Latypov, Shamil K.
• Is Part Of: RSC advances. Volume 6:Issue 33(2016)
• Page Start: 27885
• Page End: 27895
• Publication Date: 2016-03-16
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c6ra02586b
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : A new acid-catalyzed rearrangement of oxiranes for the syntheses of biologically important pharmaceutical molecules with anthranilic acid and oxalamide moieties has been discovered. Abstract : A novel one-pot synthetic approach to N 1 -(2-carboxyaryl)- N 2 -(aryl or H )oxalamides from 3-(2-nitroaryl)oxirane-2-carboxamides via the classical Meinwald rearrangement and a new rearrangement sequence has been developed. The methodology is applicable to the synthesis of N -(2-carboxyphenyl)aryloxalmonoamides from (3-(2-nitrophenyl)oxiran-2-yl)(aryl)methanones. The method is operationally simple and high yielding, thus providing a new useful formula for both anthranilic acid derivatives and oxalamides.