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)
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.
see article for more examples
quinazolinones, carbodiimides, organometallic reagents, tandem reaction, cyclization