Stereochemical studies. Part 78. Saturated heterocycles. Part 65. Synthesis and spectroscopic studies of cis-5,6-trimethylene-, and cis- and trans-5,6-tetra-and -pentamethylene-1,3-oxazinan-4-ones

F. Fülöp, G. Bernáth, P. Sohár, István Pelczer

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Abstract

N-Methyl-cis-5,6-trimethylene-, and cis- and trans-5,6-tetra- and -pentamethylene-1,3-oxazinan-4-one derivatives (15) and (16) were prepared by cyclisation, with aldehydes, of the appropriate alicyclic 2-hydroxy-1- carboxamides. In each case, formation of the new C-2 centre of chirality was found to take place stereospecifically and only the (r-5,t-2,t-6) and (r-5,c-2,c-6) diastereoisomers, respectively, were formed. The conformations of the N-methyl- and N-unsubstituted cis-trimethylene-, cis-tetramethylene-, and cis-pentamethylene-1,3-oxazinan-4-ones (13)-(16) were determined by 1H and 13C n.m.r. spectroscopy in solution. Good agreement was obtained with the earlier data established by X-ray diffraction analysis of the crystalline substances. The relative steric structure of the C-2 centre of chirality was also proved by d.n.O.e. measurements. It was found that the substituent at position 2 did not affect the conformation significantly.

Original languageEnglish
Pages (from-to)2043-2048
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1984

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Chirality
Conformations
Cyclization
Aldehydes
X ray diffraction analysis
Spectroscopy
Crystalline materials
Derivatives
cyclopropane

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Stereochemical studies. Part 78. Saturated heterocycles. Part 65. Synthesis and spectroscopic studies of cis-5,6-trimethylene-, and cis- and trans-5,6-tetra-and -pentamethylene-1,3-oxazinan-4-ones",
abstract = "N-Methyl-cis-5,6-trimethylene-, and cis- and trans-5,6-tetra- and -pentamethylene-1,3-oxazinan-4-one derivatives (15) and (16) were prepared by cyclisation, with aldehydes, of the appropriate alicyclic 2-hydroxy-1- carboxamides. In each case, formation of the new C-2 centre of chirality was found to take place stereospecifically and only the (r-5,t-2,t-6) and (r-5,c-2,c-6) diastereoisomers, respectively, were formed. The conformations of the N-methyl- and N-unsubstituted cis-trimethylene-, cis-tetramethylene-, and cis-pentamethylene-1,3-oxazinan-4-ones (13)-(16) were determined by 1H and 13C n.m.r. spectroscopy in solution. Good agreement was obtained with the earlier data established by X-ray diffraction analysis of the crystalline substances. The relative steric structure of the C-2 centre of chirality was also proved by d.n.O.e. measurements. It was found that the substituent at position 2 did not affect the conformation significantly.",
author = "F. F{\"u}l{\"o}p and G. Bern{\'a}th and P. Soh{\'a}r and Istv{\'a}n Pelczer",
year = "1984",
language = "English",
pages = "2043--2048",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
issn = "1472-7781",
publisher = "Chemical Society",

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T1 - Stereochemical studies. Part 78. Saturated heterocycles. Part 65. Synthesis and spectroscopic studies of cis-5,6-trimethylene-, and cis- and trans-5,6-tetra-and -pentamethylene-1,3-oxazinan-4-ones

AU - Fülöp, F.

AU - Bernáth, G.

AU - Sohár, P.

AU - Pelczer, István

PY - 1984

Y1 - 1984

N2 - N-Methyl-cis-5,6-trimethylene-, and cis- and trans-5,6-tetra- and -pentamethylene-1,3-oxazinan-4-one derivatives (15) and (16) were prepared by cyclisation, with aldehydes, of the appropriate alicyclic 2-hydroxy-1- carboxamides. In each case, formation of the new C-2 centre of chirality was found to take place stereospecifically and only the (r-5,t-2,t-6) and (r-5,c-2,c-6) diastereoisomers, respectively, were formed. The conformations of the N-methyl- and N-unsubstituted cis-trimethylene-, cis-tetramethylene-, and cis-pentamethylene-1,3-oxazinan-4-ones (13)-(16) were determined by 1H and 13C n.m.r. spectroscopy in solution. Good agreement was obtained with the earlier data established by X-ray diffraction analysis of the crystalline substances. The relative steric structure of the C-2 centre of chirality was also proved by d.n.O.e. measurements. It was found that the substituent at position 2 did not affect the conformation significantly.

AB - N-Methyl-cis-5,6-trimethylene-, and cis- and trans-5,6-tetra- and -pentamethylene-1,3-oxazinan-4-one derivatives (15) and (16) were prepared by cyclisation, with aldehydes, of the appropriate alicyclic 2-hydroxy-1- carboxamides. In each case, formation of the new C-2 centre of chirality was found to take place stereospecifically and only the (r-5,t-2,t-6) and (r-5,c-2,c-6) diastereoisomers, respectively, were formed. The conformations of the N-methyl- and N-unsubstituted cis-trimethylene-, cis-tetramethylene-, and cis-pentamethylene-1,3-oxazinan-4-ones (13)-(16) were determined by 1H and 13C n.m.r. spectroscopy in solution. Good agreement was obtained with the earlier data established by X-ray diffraction analysis of the crystalline substances. The relative steric structure of the C-2 centre of chirality was also proved by d.n.O.e. measurements. It was found that the substituent at position 2 did not affect the conformation significantly.

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