Stereochemical studies, 73. Saturated heterocycles, 60 - Synthesis and conformational studies of cis and trans condensed-skeleton 3-substituted-1,3-oxazine-2,4-diones

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Abstract

N-Substituted-2-carboxamido-1-cycloalkanols were cyclized with 1,1′-carbonyldiimidazole to synthesize cis- and trans-N-alkyl-, N-aralkyl- and N-aryl-2,4-dioxo tri- and tetramethyleneperhydro-1,3-oxazines. The structures of the compounds and their cis or trans ring anellation were confirmed by IR,1H- and13C-NMR spectroscopy, and the cis and trans pairs of isomers were compared to establish the predominant conformation of the flexible cis isomers. It was found that-similarly to the 1,3-oxazin-2- and -4-ones studied earlier-the "O-endo" conformers are preferred, in which the 1-oxygen atom is axial to the alicyclic ring; this is independent of the number of ring atoms in the alicycle, and of the presence of an oxazinedione ring, even though this is more flexible that the ring of oxazinones.

Original languageEnglish
Pages (from-to)857-868
Number of pages12
JournalMonatshefte fur Chemie
Volume116
Issue number6-7
DOIs
Publication statusPublished - Jun 1985

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Oxazines
Isomers
Atoms
Nuclear magnetic resonance spectroscopy
Conformations
Oxygen

Keywords

  • 1,1′-Carbonyldiimidazole
  • H-NMR
  • C-NMR
  • IR
  • Substituted 1,3-oxazine-2,4-diones with condensed skeleton

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Stereochemical studies, 73. Saturated heterocycles, 60 - Synthesis and conformational studies of cis and trans condensed-skeleton 3-substituted-1,3-oxazine-2,4-diones",
abstract = "N-Substituted-2-carboxamido-1-cycloalkanols were cyclized with 1,1′-carbonyldiimidazole to synthesize cis- and trans-N-alkyl-, N-aralkyl- and N-aryl-2,4-dioxo tri- and tetramethyleneperhydro-1,3-oxazines. The structures of the compounds and their cis or trans ring anellation were confirmed by IR,1H- and13C-NMR spectroscopy, and the cis and trans pairs of isomers were compared to establish the predominant conformation of the flexible cis isomers. It was found that-similarly to the 1,3-oxazin-2- and -4-ones studied earlier-the {"}O-endo{"} conformers are preferred, in which the 1-oxygen atom is axial to the alicyclic ring; this is independent of the number of ring atoms in the alicycle, and of the presence of an oxazinedione ring, even though this is more flexible that the ring of oxazinones.",
keywords = "1,1′-Carbonyldiimidazole, H-NMR, C-NMR, IR, Substituted 1,3-oxazine-2,4-diones with condensed skeleton",
author = "J{\'a}nos Pintye and F. F{\"u}l{\"o}p and G. Bern{\'a}th and P. Soh{\'a}r",
year = "1985",
month = "6",
doi = "10.1007/BF00809162",
language = "English",
volume = "116",
pages = "857--868",
journal = "Monatshefte fur Chemie",
issn = "0026-9247",
publisher = "Springer Wien",
number = "6-7",

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TY - JOUR

T1 - Stereochemical studies, 73. Saturated heterocycles, 60 - Synthesis and conformational studies of cis and trans condensed-skeleton 3-substituted-1,3-oxazine-2,4-diones

AU - Pintye, János

AU - Fülöp, F.

AU - Bernáth, G.

AU - Sohár, P.

PY - 1985/6

Y1 - 1985/6

N2 - N-Substituted-2-carboxamido-1-cycloalkanols were cyclized with 1,1′-carbonyldiimidazole to synthesize cis- and trans-N-alkyl-, N-aralkyl- and N-aryl-2,4-dioxo tri- and tetramethyleneperhydro-1,3-oxazines. The structures of the compounds and their cis or trans ring anellation were confirmed by IR,1H- and13C-NMR spectroscopy, and the cis and trans pairs of isomers were compared to establish the predominant conformation of the flexible cis isomers. It was found that-similarly to the 1,3-oxazin-2- and -4-ones studied earlier-the "O-endo" conformers are preferred, in which the 1-oxygen atom is axial to the alicyclic ring; this is independent of the number of ring atoms in the alicycle, and of the presence of an oxazinedione ring, even though this is more flexible that the ring of oxazinones.

AB - N-Substituted-2-carboxamido-1-cycloalkanols were cyclized with 1,1′-carbonyldiimidazole to synthesize cis- and trans-N-alkyl-, N-aralkyl- and N-aryl-2,4-dioxo tri- and tetramethyleneperhydro-1,3-oxazines. The structures of the compounds and their cis or trans ring anellation were confirmed by IR,1H- and13C-NMR spectroscopy, and the cis and trans pairs of isomers were compared to establish the predominant conformation of the flexible cis isomers. It was found that-similarly to the 1,3-oxazin-2- and -4-ones studied earlier-the "O-endo" conformers are preferred, in which the 1-oxygen atom is axial to the alicyclic ring; this is independent of the number of ring atoms in the alicycle, and of the presence of an oxazinedione ring, even though this is more flexible that the ring of oxazinones.

KW - 1,1′-Carbonyldiimidazole

KW - H-NMR

KW - C-NMR

KW - IR

KW - Substituted 1,3-oxazine-2,4-diones with condensed skeleton

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