Synthesis and detailed conformational analysis of new naphthoxazino [2,3-a]benz [c]azepine and naphthoxazino [2,3-a]thieno [3,2-c]pyridine derivatives
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...
Elmentve itt :
| Szerzők: | |
|---|---|
| Dokumentumtípus: | Cikk |
| Megjelent: |
2017
|
| Sorozat: | TETRAHEDRON
73 No. 32 |
| doi: | 10.1016/j.tet.2017.06.060 |
| mtmt: | 3268034 |
| Online Access: | http://publicatio.bibl.u-szeged.hu/12513 |
| Tartalmi kivonat: | 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. |
|---|---|
| Terjedelem/Fizikai jellemzők: | 4790-4804 |
| ISSN: | 0040-4020 |