Stereochemical studies. Part 89. Saturated heterocycles. Part 84. Preparation and nuclear magnetic resonance study of norbornane-norbornene-fused 2-phenylimino-1,3-oxazines and -thiazines

Pál Sohár, Géza Stájer, Angela E. Szabó, Ferenc Fülöp, József Szúnyog, Gábor Bernáth

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Abstract

diexo- and diendo-3-hydroxymethylbicyclo[2.2.1]hept-2-yl- and hept-5-en-2-yl-amines (1)-(4) and their N-methyl and N-benzyl derivatives with phenyl isothiocyanate furnished via thioureas (5)-(8) the condensed skeleton tricyclic 2-phenylimino-1,3-thiazines (9)-(12) and 1,3-oxazine-2-thiones (13) and (14) as by-products in acidic medium. By base-catalysed cyclization of the isothiuronium salts of (5)-(8), the 2-phenylimino-1,3-oxazines (15)-(18) were obtained. The complete series of structural and annelation isomers of the norbornanes-norbornenes and oxazines-thiazines permitted a systematic 1H and 13C n.m.r. spectroscopic study of the correlation between the spectral parameters and the structural features in this family of compounds.

Original languageEnglish
Pages (from-to)599-605
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number5
DOIs
Publication statusPublished - Jan 1 1987

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ASJC Scopus subject areas

  • Chemistry(all)

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