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Report | Regular issue | Vol 23, No. 3, 1985, pp.623-632
Published online, 1st January, 1970
DOI: 10.3987/R-1985-03-0623
A Study of the Preparation and Reactions of the Unusually Labile 5-Methyl[1,2,4]oxadiazolo[2,3-c]quinazolin-2-one

Darshan Ranganathan,* Shakti Bamezai, and P. Veeraraghavan Ramachandran

*Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India


A Π2s + Π2s + ω2s cycloaddition of 4-isocyanato-2-methyl quinazoline 3-oxide leads to the title compound, 5-methyl[1,2,4]oxadiazolo[2,3-c]quinazolin-2-one (1) . Surprisingly, the weakest bond in 1 is 4-5. Rupture of this bond takes place thermally as well as with P(OR)3 leading to the isomeric, 5-methyl[1,2,4]oxadiazolo[3,4-c]quinazolin-3-one (11). A detailed thermolytic study of 1 has given products arising from scission of the bonds 2-3, 3-4 and 4-5. The 3-4 bond is preferentially broken on photolysis of 1 in MeOH.