Stereochemical studies 130 saturated heterocycles 132. Synthesis and ring-chain tautomerism of stereoisomeric 1,3-oxazines condensed with the cyclopentane ring

Ferenc Fülöp, Kalevi Pihlaja, Jorma Mattinen, Gábor Bernáth

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

Through condensation of cis-2-hydroxymethylcyclopentylamine (3) and cis-2-amintimethylcyclopentanol (5) with aromatic aldenydes, tautomeric mixtures of 1,3-oxazines and open-chain Schift bases were obtained. The two series of compounds (4a-f, 6a-f) gave satisfactory linear correlations corresponding to log Kx = kσ+ + log Kx=w(k = 0.76 ±0.04 as shown earlier2). The ring form of the corresponding trans derivatives is present in a fairly low amount, because of the strain in the trans fusion of the cyclopentane and the six-membered hetero ring. N-Methyl substitution makes the ring form in the latter compounds stable, resulting in oxazines 12 and 14. All the cyclizations in question occurred stereospecifically.

Original languageEnglish
Pages (from-to)1863-1869
Number of pages7
JournalTetrahedron
Volume43
Issue number8
DOIs
Publication statusPublished - 1987

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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