One-pot Lewis acid catalyzed reductive N-heterocyclization of 2-nitrobenzoates: A novel approach to prepare antitumor quinazoline derivatives

ORGN 548

Sandip K Kundu, sk_kundu2003@yahoo.com1, Mathew P. D. Mahindaratne, mathewmahindaratne@yahoo.com1, and George R. Negrete, gnegrete@utsa.edu2. (1) chemistry, University of Texas at San Antonio (UTSA), One UTSA Circle, San Antonio, TX 78249, (2) Department of Chemistry, University of Texas at San Antonio, 6900 N. Loop 1604 W, San Antonio, TX 78249-0698
A highly efficient and versatile synthetic approach to prepare substituted quinazolinone derivatives, precursor nuclei for various anticancer reagents, in one-pot have been described. The reaction involves an intermolecular reductive N-heterocyclization of 2-nitrobenzoate derivatives with alkyl or aryl amides catalyzed by Lewis acids. Several transition metal Lewis acids have been examined and indium(III) acetate has showed the highest catalytic activity among them, giving sub 90% yields in formamide. For example, heating of 4,5-alkyloxy-2-nitrobenzoate in the presence of In(III) acetate in formamide effortlessly gave 6,7-alkyloxy-4-quinazolinone in 87-92% yield within 4 hours.

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007