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Note | Regular issue | Vol 63, No. 6, 2004, pp.1409-1416
Published online, 9th April, 2004
DOI: 10.3987/COM-04-10040
Synthesis and Reactivity of a New Pyranoquinoxaline

Lamouri Hammal, Mokhtar Fodili, Mohamed Amari, Nawel Khier, Bellara Nedjar-Kolli,* Chantal André, Pascal Hoffmann, and Jacques Périé

*Department of Chemistry, Paul Sabatier University, Bat 2R1 - 118 route de Narbonne - 31062 Toulouse Cedex 4, France

Abstract

3-Methyl-3,4-dihydro-1H-pyrano[3,4-b]quinoxalin-1-one (2) was prepared from a series of 3-methyl-4,5,10,11-tetrahydropyrano[4,3-b][1,5]benzo- diazepin-1(3H)-one derivatives (1) bearing various substituents at position 11. The formation of this quinoxaline is initiated by oxidation of the diazepine-4’,11’-double bond to give an unstable epoxide intermediate, followed by a ring contraction which releases a carben species that has been trapped in the presence of cyclohexene. Reactivity of this new quinoxaline (2) with various primary and secondary amines was investigated.