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

P. Sohár, G. Stájer, Angela E. Szabó, F. Fülöp, József Szúnyog, G. Bernáth

Research output: Contribution to journalArticle

11 Citations (Scopus)

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 - 1987

Fingerprint

Norbornanes
Thiazines
Oxazines
Nuclear magnetic resonance
Isothiuronium
Thiones
Thiourea
Cyclization
Isomers
Amines
Byproducts
Salts
Derivatives
2-norbornene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

@article{b92d37cc05144863ac66d3b05e602c57,
title = "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",
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.",
author = "P. Soh{\'a}r and G. St{\'a}jer and Szab{\'o}, {Angela E.} and F. F{\"u}l{\"o}p and J{\'o}zsef Sz{\'u}nyog and G. Bern{\'a}th",
year = "1987",
doi = "10.1039/P29870000599",
language = "English",
pages = "599--605",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
issn = "1470-1820",
publisher = "Royal Society of Chemistry",
number = "5",

}

TY - JOUR

T1 - 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

AU - Sohár, P.

AU - Stájer, G.

AU - Szabó, Angela E.

AU - Fülöp, F.

AU - Szúnyog, József

AU - Bernáth, G.

PY - 1987

Y1 - 1987

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=37049090339&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37049090339&partnerID=8YFLogxK

U2 - 10.1039/P29870000599

DO - 10.1039/P29870000599

M3 - Article

AN - SCOPUS:37049090339

SP - 599

EP - 605

JO - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

SN - 1470-1820

IS - 5

ER -