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Paper | Regular issue | Vol 45, No. 1, 1997, pp.95-106
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7627
Synthesis and Conformational Behaviour of 2-Phenylperhydropyrrolo[1,2-d]-[1,3,4]oxadiazine and 2-Phenylper-hydropyrido[1,2-d][1,3,4]oxadiazine; New Heterocyclic Ring Systems

Ari Rosling, Ferenc Fülöp, Reijo Sillanpää, and Jorma Mattinen*

*Department of Organic Chemistry, Åbo Akademi University, Biskopsgatan 8, FIN-20500 Åbo, Finland


Hydrazino alcohols, 1-amino-2-hydroxymethylpyrrolidine (1) and 1-amino-2-hydroxymethylpiperidine (2), were synthesized and subsequently ring closured with ethyl benzimidate to the title compounds (7) and (8), which have new ring system. Variable-temperature 1H nmr measurements, supported by X-ray analysis, indicated that pyrrolo[1,2-d][1,3,4]oxadiazine (7) exists exclusively in a cis-fused conformation (in CDCl3 at room temperature), whereas pyrido[1,2-d][1,3,4]oxadiazine (8) adopts a trans-fused conformation.