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Paper | Regular issue | Vol 43, No. 10, 1996, pp.2179-2198
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7545
1,3-Cycloaddition of Benzonitrile Oxides to Diazepines. III. 1H-1,2-Benzodiazepine

Paolo Beltrame, Enzo Cadoni, Maria M. Carnasciali, Gioanna Gelli, and Angelo Mugnoli

*Dipartimento di Scienze Chimiche, Universita di Cagliari, S.P. Monserrato-Sestu km 0.700, I-09042, Nonserrato(CA), Italy


Arylnitrile oxide (1) and 1H-1,2-benzodiazepine(2) undergo 1,3-cycloaddition reactions to give derivatives of 1,2,4-oxadiazole (3) and isoxazole (4). Aithough usually stable, the nitrile oxide partly dimerizes giving a 1,2,4-oxadiazole (7). Secondary products were also identified: for one of the (6) the structure was unambiguously determined by X-ray diffraction. Overall kinetics and product distribution were measured at 40-70°C, in mixtures of 1,1,2,2-tetrachloroethane and DMF: a set of parallel reactions was evidenced.