Synthesis and transformations of 2-(phenylhydroxymethyl)cyclohexylamines

Research output: Contribution to journalArticle

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Abstract

Diastereomeric 2-(phenylhydroxymethyl)cyclohexylamines were synthesised by reduction of 2-benzoylcyclohexylamines. (1S*,2R*)-2-Benzoylcyclohexylamine can be reduced diastereoselectively to the corresponding γ-amino alcohol with sodium borohydride; for the trans counterpart (1R*,2R*)-2-benzoylcyclohexylamine, lithium aluminium hydride was found to be a selective reducing agent. In both cases, high syn selectivities were observed. The amino alcohols were transformed to the corresponding cyclohexane-fused tetrahydro-1,3-oxazin-2-ones and -2-thiones. The γ-amino alcohols reacted with arylimidates to afford 4,5-dihydro-6H-1,3-oxazines. Their cyclization with phenyl isothiocyanate yielded 2-phenyliminotetrahydro-1,3-oxazines.

Original languageEnglish
Pages (from-to)3175-3183
Number of pages9
JournalTetrahedron
Volume57
Issue number15
DOIs
Publication statusPublished - Apr 9 2001

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Cyclohexylamines
Amino Alcohols
Oxazines
Thiones
Cyclization
Reducing Agents
oxazine 1

Keywords

  • 1,3-benzoxazines
  • 1,3-oxazines
  • Amino alcohols

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis and transformations of 2-(phenylhydroxymethyl)cyclohexylamines. / Csomós, P.; Bernáth, G.; Sohár, P.; Csámpai, A.; De Kimpe, Norbert; Fülöp, F.

In: Tetrahedron, Vol. 57, No. 15, 09.04.2001, p. 3175-3183.

Research output: Contribution to journalArticle

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abstract = "Diastereomeric 2-(phenylhydroxymethyl)cyclohexylamines were synthesised by reduction of 2-benzoylcyclohexylamines. (1S*,2R*)-2-Benzoylcyclohexylamine can be reduced diastereoselectively to the corresponding γ-amino alcohol with sodium borohydride; for the trans counterpart (1R*,2R*)-2-benzoylcyclohexylamine, lithium aluminium hydride was found to be a selective reducing agent. In both cases, high syn selectivities were observed. The amino alcohols were transformed to the corresponding cyclohexane-fused tetrahydro-1,3-oxazin-2-ones and -2-thiones. The γ-amino alcohols reacted with arylimidates to afford 4,5-dihydro-6H-1,3-oxazines. Their cyclization with phenyl isothiocyanate yielded 2-phenyliminotetrahydro-1,3-oxazines.",
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T1 - Synthesis and transformations of 2-(phenylhydroxymethyl)cyclohexylamines

AU - Csomós, P.

AU - Bernáth, G.

AU - Sohár, P.

AU - Csámpai, A.

AU - De Kimpe, Norbert

AU - Fülöp, F.

PY - 2001/4/9

Y1 - 2001/4/9

N2 - Diastereomeric 2-(phenylhydroxymethyl)cyclohexylamines were synthesised by reduction of 2-benzoylcyclohexylamines. (1S*,2R*)-2-Benzoylcyclohexylamine can be reduced diastereoselectively to the corresponding γ-amino alcohol with sodium borohydride; for the trans counterpart (1R*,2R*)-2-benzoylcyclohexylamine, lithium aluminium hydride was found to be a selective reducing agent. In both cases, high syn selectivities were observed. The amino alcohols were transformed to the corresponding cyclohexane-fused tetrahydro-1,3-oxazin-2-ones and -2-thiones. The γ-amino alcohols reacted with arylimidates to afford 4,5-dihydro-6H-1,3-oxazines. Their cyclization with phenyl isothiocyanate yielded 2-phenyliminotetrahydro-1,3-oxazines.

AB - Diastereomeric 2-(phenylhydroxymethyl)cyclohexylamines were synthesised by reduction of 2-benzoylcyclohexylamines. (1S*,2R*)-2-Benzoylcyclohexylamine can be reduced diastereoselectively to the corresponding γ-amino alcohol with sodium borohydride; for the trans counterpart (1R*,2R*)-2-benzoylcyclohexylamine, lithium aluminium hydride was found to be a selective reducing agent. In both cases, high syn selectivities were observed. The amino alcohols were transformed to the corresponding cyclohexane-fused tetrahydro-1,3-oxazin-2-ones and -2-thiones. The γ-amino alcohols reacted with arylimidates to afford 4,5-dihydro-6H-1,3-oxazines. Their cyclization with phenyl isothiocyanate yielded 2-phenyliminotetrahydro-1,3-oxazines.

KW - 1,3-benzoxazines

KW - 1,3-oxazines

KW - Amino alcohols

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