Stereochemical studies-76 saturated heterocycles-63. synthesis of cis- and trans-n-methyl- and n-benzyl-4.5- and 5,6-tetramethylenetetrahydro-1,3-oxazines; an x-ray study of n-benzyl-cis-4,5-tetramethylenetetrahydro-1,-3-oxazinium- picrate

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Abstract

- The corresponding cis- and trans-N-methyl- and N-benzyl-5,6- and 4,5-tetramethylenetetrahydro-l,3-oxazines (5a,b-8a,b)were synthesized from cis- and trans-N-methyl andN-benzyl-2- aminomethyl-1-cyclohexanols 1a,b,2a,b, from cis- and trans-N-methyl- and Nbenzyl -2-hydroxymethyl-1-cyclohexylamines(3a,b,4a,b) by reaction with formaldehyde. The aminoalcohols 1a,2a,3a,band 4a,b were prepared in considerably higher yields than in earlier procedures. NMR spectroscopy showed that the cis isomers of the synthesized oxazines were conformationally homogeneous in solution, and their preferred conformation (inside or outside) depended on the steric requirement of the groups attached to the anellation points, whereas a bulky C-2 substituent had no influence on the predominant conformation. The structure of N-benzyl-cis-4,5-tetramethylenetetrahydro-1,3-oxaziniumpicrate (7b). determined by X-ray diffraction analysis, was in agreement with the predominant N-outside conformation of the corresponding base, established by means of NMR spectroscopy.

Original languageEnglish
Pages (from-to)2053-2060
Number of pages8
JournalTetrahedron
Volume40
Issue number11
DOIs
Publication statusPublished - 1984

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Oxazines
Conformations
Magnetic Resonance Spectroscopy
Cyclohexylamines
Cyclohexanols
X-Rays
X rays
Nuclear magnetic resonance spectroscopy
X-Ray Diffraction
Formaldehyde
Isomers
X ray diffraction analysis
oxazine 1
picric acid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

@article{9efe118401ff4f44933cb9fabcd02993,
title = "Stereochemical studies-76 saturated heterocycles-63. synthesis of cis- and trans-n-methyl- and n-benzyl-4.5- and 5,6-tetramethylenetetrahydro-1,3-oxazines; an x-ray study of n-benzyl-cis-4,5-tetramethylenetetrahydro-1,-3-oxazinium- picrate",
abstract = "- The corresponding cis- and trans-N-methyl- and N-benzyl-5,6- and 4,5-tetramethylenetetrahydro-l,3-oxazines (5a,b-8a,b)were synthesized from cis- and trans-N-methyl andN-benzyl-2- aminomethyl-1-cyclohexanols 1a,b,2a,b, from cis- and trans-N-methyl- and Nbenzyl -2-hydroxymethyl-1-cyclohexylamines(3a,b,4a,b) by reaction with formaldehyde. The aminoalcohols 1a,2a,3a,band 4a,b were prepared in considerably higher yields than in earlier procedures. NMR spectroscopy showed that the cis isomers of the synthesized oxazines were conformationally homogeneous in solution, and their preferred conformation (inside or outside) depended on the steric requirement of the groups attached to the anellation points, whereas a bulky C-2 substituent had no influence on the predominant conformation. The structure of N-benzyl-cis-4,5-tetramethylenetetrahydro-1,3-oxaziniumpicrate (7b). determined by X-ray diffraction analysis, was in agreement with the predominant N-outside conformation of the corresponding base, established by means of NMR spectroscopy.",
author = "Ferenc Fol{\"o}p and G. Bern{\'a}th and G. Argay and A. K{\'a}lm{\'a}n and P. Soh{\'a}r",
year = "1984",
doi = "10.1016/S0040-4020(01)88446-5",
language = "English",
volume = "40",
pages = "2053--2060",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "11",

}

TY - JOUR

T1 - Stereochemical studies-76 saturated heterocycles-63. synthesis of cis- and trans-n-methyl- and n-benzyl-4.5- and 5,6-tetramethylenetetrahydro-1,3-oxazines; an x-ray study of n-benzyl-cis-4,5-tetramethylenetetrahydro-1,-3-oxazinium- picrate

AU - Folöp, Ferenc

AU - Bernáth, G.

AU - Argay, G.

AU - Kálmán, A.

AU - Sohár, P.

PY - 1984

Y1 - 1984

N2 - - The corresponding cis- and trans-N-methyl- and N-benzyl-5,6- and 4,5-tetramethylenetetrahydro-l,3-oxazines (5a,b-8a,b)were synthesized from cis- and trans-N-methyl andN-benzyl-2- aminomethyl-1-cyclohexanols 1a,b,2a,b, from cis- and trans-N-methyl- and Nbenzyl -2-hydroxymethyl-1-cyclohexylamines(3a,b,4a,b) by reaction with formaldehyde. The aminoalcohols 1a,2a,3a,band 4a,b were prepared in considerably higher yields than in earlier procedures. NMR spectroscopy showed that the cis isomers of the synthesized oxazines were conformationally homogeneous in solution, and their preferred conformation (inside or outside) depended on the steric requirement of the groups attached to the anellation points, whereas a bulky C-2 substituent had no influence on the predominant conformation. The structure of N-benzyl-cis-4,5-tetramethylenetetrahydro-1,3-oxaziniumpicrate (7b). determined by X-ray diffraction analysis, was in agreement with the predominant N-outside conformation of the corresponding base, established by means of NMR spectroscopy.

AB - - The corresponding cis- and trans-N-methyl- and N-benzyl-5,6- and 4,5-tetramethylenetetrahydro-l,3-oxazines (5a,b-8a,b)were synthesized from cis- and trans-N-methyl andN-benzyl-2- aminomethyl-1-cyclohexanols 1a,b,2a,b, from cis- and trans-N-methyl- and Nbenzyl -2-hydroxymethyl-1-cyclohexylamines(3a,b,4a,b) by reaction with formaldehyde. The aminoalcohols 1a,2a,3a,band 4a,b were prepared in considerably higher yields than in earlier procedures. NMR spectroscopy showed that the cis isomers of the synthesized oxazines were conformationally homogeneous in solution, and their preferred conformation (inside or outside) depended on the steric requirement of the groups attached to the anellation points, whereas a bulky C-2 substituent had no influence on the predominant conformation. The structure of N-benzyl-cis-4,5-tetramethylenetetrahydro-1,3-oxaziniumpicrate (7b). determined by X-ray diffraction analysis, was in agreement with the predominant N-outside conformation of the corresponding base, established by means of NMR spectroscopy.

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JF - Tetrahedron

SN - 0040-4020

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ER -