The reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with methanesulfonyl chloride or pph3-cbr4

Yulia V. Khoroshunova, Denis A. Morozov, Andrey I. Taratayko, Sergey A. Dobrynin, Ilia V. Eltsov, Tatyana V. Rybalova, Yulia S. Sotnikova, Dmitriy N. Polovyanenko, Nargiz B. Asanbaeva, Igor A. Kirilyuk

Результат исследования: Научные публикации в периодических изданияхстатьярецензирование

Аннотация

Activation of a hydroxyl group towards nucleophilic substitution via reaction with me-thanesulfonyl chloride or PPh3-CBr4 system is a commonly used pathway to various functional derivatives. The reactions of (5R(S),6R(S))-1-X-6-(hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes 1a–d (Х = O·; H; OBn, OBz) with MsCl/NR3 or PPh3-CBr4 were studied. Depending on substituent X, the reaction afforded hexahy-dro-1H,6H-cyclopenta[c]pyrrolo[1,2-b]isoxazole (2) (for X = O), a mixture of 2 and octahydrocy-clopenta[c]azepines (4–6) (for X = OBn, OBz), or perhydro-cyclopenta[2,3]azeto[1,2-a]pyrrol (3) (for X = H) derivatives. Alkylation of the latter with MeI with subsequent Hofmann elimination afforded 2,3,3-trimethyl-1,2,3,4,5,7,8,8a-octahydrocyclopenta[c]azepine with 56% yield.

Язык оригиналаанглийский
Номер статьи6000
ЖурналMolecules
Том26
Номер выпуска19
DOI
СостояниеОпубликовано - 1 окт 2021

Предметные области OECD FOS+WOS

  • 1.04 ХИМИЧЕСКИЕ НАУКИ
  • 1.06.CQ БИОХИМИЯ И МОЛЕКУЛЯРНАЯ БИОЛОГИЯ

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