Journal
TETRAHEDRON
Volume 73, Issue 32, Pages 4790-4804Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.06.060
Keywords
Aminonaphthol; DFT modelling; Mannich reaction; Microwave reaction; ortho-quinonemethide
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Funding
- Hungarian Research Foundation (OTKA) [K115731]
- Ministry of National Research Development and Innovation Office [GINOP-2.3.2-15-2016-00038]
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New naphth[1,3]oxazino-benzazepines and -thienopyridines were synthesized using a modified Mannich-type synthetic pathway by the reaction of 4,5-dihydro-3H-benz[c]azepine or 6,7-dihydrothieno [3,2-clpyridine and different substituted aminonaphthols. Reaction conditions were optimized using microwave irradiation, with relatively short reaction times and a temperature of 80 degrees C. The formation of undesired naphthoxazine by-products made the separation/purification of the products challenging, therefore the reactions were repeated and systematically studied, starting from secondary and tertiary aminonaphthol derivatives, when the isolation of an ortho-quinonemethide structure occurred unexpectedly. Scope and limitations of its formation were also investigated. Conformational studies including ring inversion of a selection of the novel polyheterocycles were performed using NMR methods and supplementary DFT modelling. (C) 2017 Elsevier Ltd. All rights reserved.
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