Rearrangement of 2-azanorbornenes to tetrahydrocyclopenta[c]pyridines under the action of activated alkynes – A short pathway for construction of the altemicidin core

A simple approach to a series of 2,4a,7,7a-tetrahydro-1H-cyclopenta[c]pyridines was proposed on the basis of the amino-Claisen rearrangement of readily accessible 2-azabicyclo[2.2.1]hept-5-enes under the action of dialkyl acetylenedicarboxylates, methyl propiolate or propiolamide. The rearrangement is highly diastereoselective and leads to the formation of only one isomer with cis-annulation of the five- and six-membered rings in satisfactory yields. Using the developed method, close analogs of the altemicidin and SB-203207 cores were synthesized. © 2017 Elsevier Ltd

Авторы
Nasirova D.K. 1 , Malkova A.V. 1 , Polyanskii K.B. 1 , Yankina K.Y. 1 , Amoyaw P.N.-A.2 , Kolesnik I.A.3 , Kletskov A.V.3 , Godovikov I.A.4 , Nikitina E.V. 1 , Zubkov F.I. 1
Редакторы
-
Журнал
Издательство
Elsevier Ltd
Номер выпуска
46
Язык
Английский
Страницы
4384-4387
Статус
Опубликовано
Подразделение
-
Номер
-
Том
58
Год
2017
Организации
  • 1 Department of Organic Chemistry, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
  • 2 Division of Liberal Arts and Sciences, State University of New York at Delhi, Delhi, NY 13753, United States
  • 3 Institute of Physical Organic Chemistry, National Academy of Sciences, 13 Surganov St., Minsk, 220072, Belarus
  • 4 A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, 28 Vavilova St., Moscow, 119991, Russian Federation
Ключевые слова
2-Azabicyclo[2.2.1]hept-5-ene; 2-Azanorbornene; Altemicidin; Amino-Claisen rearrangement; Cyclopenta[c]pyridine; DMAD
Дата создания
19.10.2018
Дата изменения
19.10.2018
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/5180/