Easy construction of furo[2,3-f]isoindole core by the IMDAV reaction between 3-(furyl)allylamines and α,β-unsaturated acid anhydrides

The vinylogues of furfurylamines, easily available in two steps from furylacroleins (3-(furyl)allylamines), were studied in a tandem N-acylation/intramolecular [4+2] cycloaddition with maleic, pyrocinchonic, and citraconic anhydrides, as well as furylacryloyl and cinnamoyl chlorides. By using a domino reaction of 3-(furyl)allylamines and α,β-unsaturated acid anhydrides under mild conditions, various hexahydro-4H-furo[2,3-f]isoindoles and their carboxyl derivatives were synthesized efficiently. The domino sequence includes three steps: acylation of the nitrogen atom in 3-(furyl)allylamines, intramolecular Diels-Alder cycloaddition in the resulting N-acyl vinylfurans (IMDAV reaction), and prototropic shift of the adducts followed by recovery of aromaticity of the furan nucleus. The key step, IMDAV reaction, leads to the target products, furo[2,3-f]isoindoles, diastereoselectively and with relatively high yields. © 2016 Elsevier Ltd. All rights reserved.

Авторы
Zubkov F.I. 1 , Zaytsev V.P. 1 , Mertsalov D.F. 1 , Nikitina E.V. 1 , Horak Y.I.2 , Lytvyn R.Z.2 , Homza Y.V.2 , Obushak M.D.2 , Dorovatovskii P.V.3 , Khrustalev V.N. 4, 5 , Varlamov A.V. 1
Журнал
Номер выпуска
18
Язык
Английский
Страницы
2239-2253
Статус
Опубликовано
Том
72
Год
2016
Организации
  • 1 Department of Organic Chemistry, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
  • 2 Department of Organic Chemistry, Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv, 79005, Ukraine
  • 3 NRC Kurchatov Institute, 1 Acad. Kurchatov Sq., Moscow, 123182, Russian Federation
  • 4 Department of Inorganic Chemistry, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
  • 5 X-ray Structural Centre, A. N. Nesmeyanov Institute of Organoelement Compounds of RAS, 28 Vavilov St., Moscow, 119991, Russian Federation
Ключевые слова
Cycloaddition; Diels-Alder; Furan; IMDAV; Isoindole
Дата создания
19.10.2018
Дата изменения
19.10.2018
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/3928/
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