A two-stage synthesis of 8,10a-epoxypyrido[2,1-a]isoindoles: Stereochemistry of the [4+2] cycloaddition of maleic anhydride with 2,6-difurylpiperidin-4-ones

A new straightforward synthesis of 8,10a-epoxypyrido[2,1-a]isoindoles and their 7-carboxylic acids from 2,6-difurylsubstituted piperidin-4-ones and maleic anhydride or acryloyl chloride via the intramolecular Diels-Alder reaction has been demonstrated. It has been shown that a one-stage synthesis of the title compounds can be performed under mild conditions and with high levels of regio-and stereoselectivity from easily accessible 2-furylpiperidines. © Georg Thieme Verlag Stuttgart - New York.

Authors
Zubkov F.I. 1 , Airiyan I.K. 1 , Turchin K.F.2 , Zaytsev V.P. 1 , Gurbanov A.V.3 , Maharramov A.M.3 , Khrustalev V.N.4 , Peregudov A.S.4 , Nikitina E.V. 1 , Varlamova A.V. 1
Editors
-
Journal
Publisher
-
Number of issue
24
Language
English
Pages
4235-4255
Status
Published
Department
-
Number
Z13609SS
Volume
-
Year
2009
Organizations
  • 1 Organic Chemistry Department, Russian Peoples Friendship University, Miklukho-Maklaya St. 6, Moscow 117198, Russian Federation
  • 2 Center of Drugs Chemistry, All-Russian Institute for Chemical and Pharmaceutical Research, Zubovskaya St. 7, Moscow 119815, Russian Federation
  • 3 Baku State University, Z. Khalilov St. 23, Baku 1148, Azerbaijan
  • 4 Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov St. 28, Moscow 119991, Russian Federation
Keywords
2,6-difurylpiperidin-4-ones; Furans; IMDAF; Intramolecular Diels-Alder furan reaction; Pyrido[2,1-a]isoindoles; Stereoselective synthesis
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/2885/