Stereochemical studies-XVII. Cyclic aminoalcohols and related compounds-IX synthesis and NMR study of stereoisomeric cis- and trans-tetramethylene- and pentamethylene-1,3-oxazine-2-ones

G. Bernáth, Gy Göndös, K. Kovács, P. Sohár

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Abstract

Isomeric tetramethylene- and pentamethylene-1,3-oxazine-2-ones (9-12 and 13-16) have been synthesized, derived from cis- and trans-2-aminomethylcyclohexanol (1,2), cis- and trans-2-hydroxymethylcyclohexylamine (3,4) and from the corresponding cycloheptane analogues (5-8), respectively. The stereospecific synthesis of the aminoalcohols 5-8 is described. A comparative NMR analysis of 13-16 and the tetramethylene analogues (9-12) is given.

Original languageEnglish
Pages (from-to)981-984
Number of pages4
JournalTetrahedron
Volume29
Issue number7
DOIs
Publication statusPublished - 1973

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Cycloheptanes
Oxazines
Nuclear magnetic resonance
oxazine 1

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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title = "Stereochemical studies-XVII. Cyclic aminoalcohols and related compounds-IX synthesis and NMR study of stereoisomeric cis- and trans-tetramethylene- and pentamethylene-1,3-oxazine-2-ones",
abstract = "Isomeric tetramethylene- and pentamethylene-1,3-oxazine-2-ones (9-12 and 13-16) have been synthesized, derived from cis- and trans-2-aminomethylcyclohexanol (1,2), cis- and trans-2-hydroxymethylcyclohexylamine (3,4) and from the corresponding cycloheptane analogues (5-8), respectively. The stereospecific synthesis of the aminoalcohols 5-8 is described. A comparative NMR analysis of 13-16 and the tetramethylene analogues (9-12) is given.",
author = "G. Bern{\'a}th and Gy G{\"o}nd{\"o}s and K. Kov{\'a}cs and P. Soh{\'a}r",
year = "1973",
doi = "10.1016/0040-4020(73)80049-3",
language = "English",
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pages = "981--984",
journal = "Tetrahedron",
issn = "0040-4020",
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T1 - Stereochemical studies-XVII. Cyclic aminoalcohols and related compounds-IX synthesis and NMR study of stereoisomeric cis- and trans-tetramethylene- and pentamethylene-1,3-oxazine-2-ones

AU - Bernáth, G.

AU - Göndös, Gy

AU - Kovács, K.

AU - Sohár, P.

PY - 1973

Y1 - 1973

N2 - Isomeric tetramethylene- and pentamethylene-1,3-oxazine-2-ones (9-12 and 13-16) have been synthesized, derived from cis- and trans-2-aminomethylcyclohexanol (1,2), cis- and trans-2-hydroxymethylcyclohexylamine (3,4) and from the corresponding cycloheptane analogues (5-8), respectively. The stereospecific synthesis of the aminoalcohols 5-8 is described. A comparative NMR analysis of 13-16 and the tetramethylene analogues (9-12) is given.

AB - Isomeric tetramethylene- and pentamethylene-1,3-oxazine-2-ones (9-12 and 13-16) have been synthesized, derived from cis- and trans-2-aminomethylcyclohexanol (1,2), cis- and trans-2-hydroxymethylcyclohexylamine (3,4) and from the corresponding cycloheptane analogues (5-8), respectively. The stereospecific synthesis of the aminoalcohols 5-8 is described. A comparative NMR analysis of 13-16 and the tetramethylene analogues (9-12) is given.

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VL - 29

SP - 981

EP - 984

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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