Conformational analysis of stereoisomeric dodecahydropyrido[2,1-b]-quinazolin-11-ones

Gábor Tóth, F. Fülöp, G. Bernáth, Kálmán Simon, I. Hermecz, Zoltán Mészáros

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The structures and conformations of dodecahydropyrido[2,1-b]quinazolin-11-one diastereoisomers, prepared from the corresponding decahydro-derivatives by hydrogenation, have been established by 13C and 1H n.m.r. spectroscopy. Evidence has been found that the situations of the hydrogen atoms attached to the angular C-4a, C-11a, and C-5a correspond to the α, β, α; α, α, α; and α, α, β configurations. In the cis α, α, α product the conformational equilibrium is shifted towards that conformer in which N-5 is axial with respect to ring A, whereas in the α, α, β product the C=O group assumes the axial position. The configuration of the lone pair of N-5 has been determined as well.

Original languageEnglish
Pages (from-to)237-240
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number3
DOIs
Publication statusPublished - 1983

Fingerprint

Hydrogenation
Conformations
Hydrogen
Spectroscopy
Derivatives
Atoms

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Conformational analysis of stereoisomeric dodecahydropyrido[2,1-b]-quinazolin-11-ones. / Tóth, Gábor; Fülöp, F.; Bernáth, G.; Simon, Kálmán; Hermecz, I.; Mészáros, Zoltán.

In: Journal of the Chemical Society, Perkin Transactions 2, No. 3, 1983, p. 237-240.

Research output: Contribution to journalArticle

@article{2d34a16983994ef68747fb1ab512caf0,
title = "Conformational analysis of stereoisomeric dodecahydropyrido[2,1-b]-quinazolin-11-ones",
abstract = "The structures and conformations of dodecahydropyrido[2,1-b]quinazolin-11-one diastereoisomers, prepared from the corresponding decahydro-derivatives by hydrogenation, have been established by 13C and 1H n.m.r. spectroscopy. Evidence has been found that the situations of the hydrogen atoms attached to the angular C-4a, C-11a, and C-5a correspond to the α, β, α; α, α, α; and α, α, β configurations. In the cis α, α, α product the conformational equilibrium is shifted towards that conformer in which N-5 is axial with respect to ring A, whereas in the α, α, β product the C=O group assumes the axial position. The configuration of the lone pair of N-5 has been determined as well.",
author = "G{\'a}bor T{\'o}th and F. F{\"u}l{\"o}p and G. Bern{\'a}th and K{\'a}lm{\'a}n Simon and I. Hermecz and Zolt{\'a}n M{\'e}sz{\'a}ros",
year = "1983",
doi = "10.1039/P29830000237",
language = "English",
pages = "237--240",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
issn = "1470-1820",
publisher = "Royal Society of Chemistry",
number = "3",

}

TY - JOUR

T1 - Conformational analysis of stereoisomeric dodecahydropyrido[2,1-b]-quinazolin-11-ones

AU - Tóth, Gábor

AU - Fülöp, F.

AU - Bernáth, G.

AU - Simon, Kálmán

AU - Hermecz, I.

AU - Mészáros, Zoltán

PY - 1983

Y1 - 1983

N2 - The structures and conformations of dodecahydropyrido[2,1-b]quinazolin-11-one diastereoisomers, prepared from the corresponding decahydro-derivatives by hydrogenation, have been established by 13C and 1H n.m.r. spectroscopy. Evidence has been found that the situations of the hydrogen atoms attached to the angular C-4a, C-11a, and C-5a correspond to the α, β, α; α, α, α; and α, α, β configurations. In the cis α, α, α product the conformational equilibrium is shifted towards that conformer in which N-5 is axial with respect to ring A, whereas in the α, α, β product the C=O group assumes the axial position. The configuration of the lone pair of N-5 has been determined as well.

AB - The structures and conformations of dodecahydropyrido[2,1-b]quinazolin-11-one diastereoisomers, prepared from the corresponding decahydro-derivatives by hydrogenation, have been established by 13C and 1H n.m.r. spectroscopy. Evidence has been found that the situations of the hydrogen atoms attached to the angular C-4a, C-11a, and C-5a correspond to the α, β, α; α, α, α; and α, α, β configurations. In the cis α, α, α product the conformational equilibrium is shifted towards that conformer in which N-5 is axial with respect to ring A, whereas in the α, α, β product the C=O group assumes the axial position. The configuration of the lone pair of N-5 has been determined as well.

UR - http://www.scopus.com/inward/record.url?scp=37049095356&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37049095356&partnerID=8YFLogxK

U2 - 10.1039/P29830000237

DO - 10.1039/P29830000237

M3 - Article

AN - SCOPUS:37049095356

SP - 237

EP - 240

JO - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

SN - 1470-1820

IS - 3

ER -