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Paper | Regular issue | Vol 45, No. 5, 1997, pp.927-942
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7760
2-[Arylamino(imino)]perhydropyrido-[1,2-d][1,3,4]oxadiazine and 2-[Aryl-amino(imino)]-perhydropyrrolo[1,2-d]-[1,3,4]oxadiazine: Heterocyclic Ring Systems Involving a Bridge-Head Nitrogen

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

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

Abstract

Hydrazino alcohols (1 - 4) were converted with phenyl or 4-chlorophenyl isothiocyanate into their thiourea derivatives (5a,b, 6a,b, 9a,b and 10a,b) which then were cyclized by treatment with methyl iodide and alkali to furnish 2-[arylamino(imino)]perhydropyrido[1,2-d][1,3,4]oxadiazines (7a,b) and perhydropyrrolo[1,2-d][1,3,4]oxadiazines (12a,b) and their 2-arylimino-3N-methyl derivatives (8a,b and 13b). The nmr spectra and X-ray crystallographic analysis indicated that the 1,3,4-oxadiazines adopt rigid cis- or trans-fused ring conformations, depending on the parent ring size and the 3N-substituent. It was found that in the unsubstituted 1,3,4-oxadiazines (7a,b and 12a,b) involving a potential tautomeric equilibrium. The amino form is most likely to predominate.