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Synlett 2016; 27(05): 782-788
DOI: 10.1055/s-0035-1560383
DOI: 10.1055/s-0035-1560383
letter
Unusual Acid- and Base-Catalyzed C–N Bond Formation Approach through Reaction of Chromonyl Meldrum’s Acid and Nitrogen Binucleophiles
Further Information
Publication History
Received: 22 August 2015
Accepted after revision: 20 October 2015
Publication Date:
30 November 2015 (online)
Abstract
Reaction of chromonyl Meldrum’s acid and N-substituted 2-aminobenzamides was studied in the presence of acidic and basic catalysts. The use of methanesulfonic acid as a catalyst in this reaction led to the synthesis of chromonyl quinazolinones through employing Meldrum’s acid as a carbon leaving group. However, in the presence of basic catalyst, this reaction gave functionalized 2-pyridones.
Keywords
chromonyl Meldrum’s acid - binucleophile - acid catalysis - base catalysis - chromonyl quinazolinines - domino Michael–elimination–cyclization reaction - functionalized 2-pyridonesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560383. Copies of 1H NMR, 13C NMR for compound 3a and 1H NMR, 13C NMR, IR, HRMS spectra for compounds 7a–n and 8a–d, and X-ray crystal data for compounds 7c and 7k are included.
- Supporting Information