Synthesis, reactions and stereochemistry of 3-hydroxymethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one and some perhydrogenated derivatives

F. Fülöp, Kalevi Pihlaja, Imre Huber, G. Bernáth, Béla Ribár, G. Argay, A. Kálmán

Research output: Contribution to journalArticle

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Abstract

3-Hydroxymethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one and a number of its perhydrogenated derivatives were prepared from the corresponding 2-hydroxycarboxamides by treatment with a formaldehyde/formic acid mixture. Thermal decomposition of the 3-hydroxymethyl derivatives led to the previously unknown parent compounds. With one exception (14), both in the N-unsubstituted (16-18) and in the N-substituted (7-15) cyclopentane- and cyclohexane-fused derivatives the oxazinone ring predominantly attains a single half-chair conformation.

Original languageEnglish
Pages (from-to)4963-4970
Number of pages8
JournalTetrahedron
Volume48
Issue number23
DOIs
Publication statusPublished - Jun 5 1992

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formic acid
Cyclopentanes
Stereochemistry
Formaldehyde
Hot Temperature
Derivatives
Conformations
Pyrolysis
Cyclohexane

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis, reactions and stereochemistry of 3-hydroxymethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one and some perhydrogenated derivatives. / Fülöp, F.; Pihlaja, Kalevi; Huber, Imre; Bernáth, G.; Ribár, Béla; Argay, G.; Kálmán, A.

In: Tetrahedron, Vol. 48, No. 23, 05.06.1992, p. 4963-4970.

Research output: Contribution to journalArticle

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AU - Pihlaja, Kalevi

AU - Huber, Imre

AU - Bernáth, G.

AU - Ribár, Béla

AU - Argay, G.

AU - Kálmán, A.

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