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Publikācija: Contrasting Behaviour of NBS towards 1

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Nosaukums oriģinālvalodā Contrasting Behaviour of NBS towards 1,4-Dihydro-Benzothieno[3,2-B]Pyridine 5,5-Dioxides and 4,5-Dihydro-1H-Indeno[1,2-B]Pyridines
Pētniecības nozare 1. Dabaszinātnes
Pētniecības apakšnozare 1.4. Ķīmija
Autori B. Cekavicus
B. Vīgante
M. Rucins
K. Birkmane
M. Petrova
Sergejs Beļakovs
L. Zuka
A. Plotniece
K. Pajuste
M. Gosteva
A. Sobolev
Atslēgas vārdi Polycyclic 1,4-dihydropyridines; Cyclisation; Bromination; Oxidation; N-Bromosuccinimide
Anotācija Polycyclic 1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxides and 4,5-dihydro-1H-indeno[1,2-b]pyridines having ester or cyano group at the position 3 of dihydropyridine ring have been synthesised. Reactivity of N-bromosuccinimide (NBS) towards polycyclic 1,4-dihydropyridine derivatives has been investigated. It has been found that 1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxides are easily oxidised with NBS in methanol at rt in high yields, whereas 4,5-dihydro-1H-indeno[1,2-b]pyridines in reaction with NBS in methanol are brominated at 4a position affording stable 4a-bromo-4a,5-dihydroindeno[1,2-b]pyridine-3-carboxylates or unstable 3-carbonitriles, which rapidly undergo dehydrobromination reaction leading to the corresponding 5H-indeno[1,2-b]pyridine-3-carbonitriles.
DOI: 10.1016/j.tet.2013.04.060
Hipersaite: http://www.sciencedirect.com/science/article/pii/S004040201300598X 
Atsauce Cekavicus, B., Vigante, B., Rucins, M., Birkmane, K., Petrova, M., Beļakovs, S., Zuka, L., Plotniece, A., Pajuste, K., Gosteva, M., Sobolev, A. Contrasting Behaviour of NBS towards 1,4-Dihydro-Benzothieno[3,2-B]Pyridine 5,5-Dioxides and 4,5-Dihydro-1H-Indeno[1,2-B]Pyridines. Tetrahedron , 2013, Vol.69, Iss.26, 5550.-5557.lpp. ISSN 0040-4020. Pieejams: doi:10.1016/j.tet.2013.04.060
ID 17030