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Synthesis and Conformational Analysis of Naphthoxazine-Fused Phenanthrene Derivatives.

ABSTRACT: The synthesis of new phenanthr[9,10-e][1,3]oxazines was achieved by the direct coupling of 9-phenanthrol with cyclic imines in the modified aza-Friedel-Crafts reaction followed by the ring closure of the resulting bifunctional aminophenanthrols with formaldehyde. Aminophenanthrol-type Mannich bases were synthesised and transformed to phenanthr[9,10-e][1,3]oxazines via [4 + 2] cycloaddition. Detailed NMR structural analyses of the new polyheterocycles as well as conformational studies including Density Functional Theory (DFT) modelling were performed. The relative stability of ortho-quinone methides (o-QMs) was calculated, the geometries obtained were compared with the experimentally determined NMR structures, and thereby, the regioselectivity of the reactions has been assigned.

SUBMITTER: Belasri K

PROVIDER: S-EPMC7321197 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Synthesis and Conformational Analysis of Naphthoxazine-Fused Phenanthrene Derivatives.

Belasri Khadija K Topal Leila L Heydenreich Matthias M Koch Andreas A Kleinpeter Erich E Fülöp Ferenc F Szatmári István I

Molecules (Basel, Switzerland) 20200528 11

The synthesis of new phenanthr[9,10-e][1,3]oxazines was achieved by the direct coupling of 9-phenanthrol with cyclic imines in the modified aza-Friedel-Crafts reaction followed by the ring closure of the resulting bifunctional aminophenanthrols with formaldehyde. Aminophenanthrol-type Mannich bases were synthesised and transformed to phenanthr[9,10-e][1,3]oxazines via [4 + 2] cycloaddition. Detailed NMR structural analyses of the new polyheterocycles as well as conformationa ...[more]

PMID: 32481689

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