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Paper | Regular issue | Vol 45, No. 7, 1997, pp.1289-1297
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7798
Aziridination and 1,3-Dipolar Cycloaddition of 2,6-Dibenzylidenecyclohexanone

Hassan A. Albar,* John Fawcett, and D. R. Russell

*Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21413 P.O.Box 9028, Saudi Arabia

Abstract

2,6-Dibenzylidenecyclohexanone (1), 5-benzylidene-1-(2-alkyl-3,4-dihydro-4-oxoquinazolin-3-yl)-4-oxo-2-phenyl-1-azaspiro[2,5]octane (3) and 7-benzylidene-1,3,4-triphenyl-6-oxo-1,2-diazaspiro[4,5]decane (10) were aziridinated using 3-acetoxyamino-2-alkylquinazolin-4(3H)-ones (2a-c) to form 1,6-di-(2-alkyl-3,4-dihydro-4-oxoquinazolin-3-yl)-4-oxo-2,7-diphenyl-1,6-diazadispiro[2,1,2,3]decane (4a-c) and 8-(2-alkyl-3,4-dihydro-4-oxoquinazolin-3-yl)-1,3,4,9-tetraphenyl-6-oxo-1,2,8-triazadispiro[2,1,4,3]dodecane derivatives (9a) and (9b) as single stereoisomers. The stereostructures of 3a and 9a were confirmed by X-Ray crystallography.