AN UNUSUAL REARRANGEMENT INVOLVING 5-BROMO-1-PHENYLPYRIDONE DURING ITS METHYL CROSS COUPLING WITH TURBO-GRIGNARD REAGENT, LEADING TO A 5-BROMOPYRIDONE-FUSED SEVEN-MEMBERED CARBOCYCLIC RING

Авторы

  • Eliezer Falb Discovery & Product Development, Global Innovative R&D, Teva Pharmaceutical Industries Ltd., 12 Hatrufa St., PO Box 8077, Kiryat Sapir 42504 Netanya
  • Konstantin Ulanenko Discovery & Product Development, Global Innovative R&D, Teva Pharmaceutical Industries Ltd., 12 Hatrufa St., PO Box 8077, Kiryat Sapir 42504 Netanya
  • Andrey Tor Discovery & Product Development, Global Innovative R&D, Teva Pharmaceutical Industries Ltd., 12 Hatrufa St., PO Box 8077, Kiryat Sapir 42504 Netanya
  • Michal Afri Department of Chemistry, Bar-Ilan University, Ramat Gan 52900
  • Hugo Gottlieb Department of Chemistry, Bar-Ilan University, Ramat Gan 52900
  • Alfred Hassner Department of Chemistry, Bar-Ilan University, Ramat Gan 52900

DOI:

https://doi.org/10.1007/3875

Ключевые слова:

cyclohepta[c]pyridin-1-one, 3, 4-dihydropyridin-2(1H)-one, 3-halo-1-phenylpyridone, turbo-Grignard reagent

Аннотация

The structure of a cyclohepta[c]pyridin-1-one, a product of an unusual transformation, isolated during a turbo-Grignard reagentpromoted methyl cross coupling to 5-bromo-1-phenyl-2-pyridone, was determined by 1H and 13C NMR, COSY, and high-resolution MS, as well as computer modeling. Its formation suggests a remarkable nucleophilic attack at the α-position to the pyridone carbonyl group. A rational pathway is presented.

Биографии авторов

Eliezer Falb, Discovery & Product Development, Global Innovative R&D, Teva Pharmaceutical Industries Ltd., 12 Hatrufa St., PO Box 8077, Kiryat Sapir 42504 Netanya

Chemical Project Leader

Konstantin Ulanenko, Discovery & Product Development, Global Innovative R&D, Teva Pharmaceutical Industries Ltd., 12 Hatrufa St., PO Box 8077, Kiryat Sapir 42504 Netanya

Researcher

Andrey Tor, Discovery & Product Development, Global Innovative R&D, Teva Pharmaceutical Industries Ltd., 12 Hatrufa St., PO Box 8077, Kiryat Sapir 42504 Netanya

Researcher

Michal Afri, Department of Chemistry, Bar-Ilan University, Ramat Gan 52900

Researcher

Hugo Gottlieb, Department of Chemistry, Bar-Ilan University, Ramat Gan 52900

NMR Specialist

Alfred Hassner, Department of Chemistry, Bar-Ilan University, Ramat Gan 52900

Prof. for Chemistry

Department of Chemistry, Bar-Ilan University, Ramat Gan 52900, Israel

Опубликован

2017-11-03

Выпуск

Раздел

Оригинальные статьи