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Functionalized Carbodiimide Mediated Synthesis of 2,3-Disubstituted Quinazolin-4(3H)-ones via the Tandem Strategy of C-Nucleophilic Addition and Intramolecular NH-Substitution Cyclization

Hayato Nakano, Noriki Kutsumura, Takao Saito*

*Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Email: tsaitors.kagu.tus.ac.jp

H. Nakano, N. Kutsumura, T. Saito, Synthesis, 2012, 44, 3179-3184.

DOI: 10.1055/s-0032-1316773 (free Supporting Information)


Abstract

Key to a facile synthesis of 2,3-disubstituted quinazolin-4(3H)-ones is a tandem strategy involving introduction of a 2-substituent and construction of the quinazolinone framework via C-nucleophilic addition to a carbodiimide cumulenic carbon followed by intramolecular nucleophilic substitution by the newly formed NH moiety at the proximal ester group.


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Key Words

quinazolinones, carbodiimides, organometallic reagents, tandem reaction, cyclization


ID: J66-Y2012-3380