Formation of 1,3-perhydrobenzoxazines and their N-methyl derivatives. A comparative study

Aija Parkkinen, Ferenc Fülöp, Kalevi Pihlaja

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Abstract

The formation of perhydro-1,3-oxazine derivatives (3) through the cyclization reaction of p-nitrobenzaldehyde with cis- (1) and trans-2-aminomethyl-1-cyclohexanol (2) or with their N-methyl derivatives (1m and 2m) were studied by 1H NMR spectroscopy in CDCl3. The reactions with 1 and 2 proceeded via open-chain intermediates whereas those with 1m and 2m showed no signs of these intermediates. The cyclization reactions of the N-methyl substituted cyclohexanols (1m and 2m) were much faster than those of the corresponding hydroxymethylcyclohexylamines studied earlier. The cyclization of 1 was kinetically controlled but in much lesser extent than the corresponding reaction with cis-2-hydroxymethyl-1-cyclohexylamine. These results confirmed that the cyclization reactions of p-nitrobenzaldehyde with 2-aminomethyl-1-cyclohexanols and their N-methyl derivatives parallel to those with 2-hydroxymethyl-1-cyclohexylamines and their N-methyl derivatives are not usually diastereospecific.

Original languageEnglish
Pages (from-to)2229-2236
Number of pages8
JournalTetrahedron
Volume47
Issue number12-13
DOIs
Publication statusPublished - 1991

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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