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Paper | Regular issue | Vol 24, No. 11, 1986, pp.3087-3095
Published online, 1st January, 1970
DOI: 10.3987/R-1986-11-3087
Dihydroisoxazolo[2,3-d][1,4]benzodiazepine Ring System: Stereochemistry and Conformation

Giuseppe Capozzi,* Rosaria Ottanà, Giovanni Romeo, and Nicola Uccella

*Dipartimento di Chimica Organica "Ugo Schiff", Università di Firenze, Via Gino Capponi 9, I-50121 Firenze, Italy


The configurational properties of dihydroisoxazolo[2,3-d][1,4]benzodiazepine derivatives, obtained by 1,3-dipolar cycloaddition between chlordiazepoxide and various substituted alkynes, have been determined by 1H nmr spectroscopy, largely by computer-simulation of lanthanide induced shifts (LIS). Cycloadducts exist in solution as a 3:2 mixture of two lnterconvertible diastereoisomers, which are the result of the heptaatomic ring mobility. The stereochemistry of examined derivatives has been found appropriate to determine the further rearrangement to pyrrole-fused quinoxalines, observed in this new tricyclic system.