The intramolecular Diels-Alder vinylfuran (IMDAV) reaction: a short approach to aza-analogues of pinguisane-type sesquiterpenes

Abstract The reaction of readily accessible (3-furyl)allylamines with maleic anhydride, followed by a domino sequence involving acylation/cycloaddition/proton shift steps, led to the formation of furo[2,3-f]isoindoles - the aza-analogs of pinguisane-type sesquiterpenes. The key intramolecular Diels-Alder vinylfuran (IMDAV) reaction proceeded under mild conditions, with high levels of diastereoselectivity and satisfactory yields. © 2015 Elsevier Ltd.

Authors
Horak Y.I.1 , Lytvyn R.Z.1 , Homza Y.V.1 , Zaytsev V.P. 2 , Mertsalov D.F. 2 , Babkina M.N. 2 , Nikitina E.V. 2 , Lis T.3 , Kinzhybalo V.4 , Matiychuk V.S.1 , Zubkov F.I. 2 , Varlamov A.V. 2 , Obushak M.D.1
Journal
Tetrahedron Letters
Publisher
Elsevier Ltd
Number of issue
30
Language
English
Pages
4499-4501
Status
Published
Link
External link
DOI
10.1016/j.tetlet.2015.05.115
Number
46387
Volume
56
Year
2015
Organizations
  • 1 Department of Organic Chemistry, Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv, 79005, Ukraine
  • 2 Department of Organic Chemistry, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
  • 3 Faculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, 50-383 Wrocław, Poland
  • 4 Institute of Low Temperature and Structure Research, Okolna 2, Wrocław, 50-422, Poland
Keywords
Diels-Alder reaction; Furan; Furo[2,3-f]isoindoles; IMDAV; Pinguisane-type sesquiterpenes; [2+4] cycloaddition
Date of creation
19.10.2018
Date of change
13.08.2021
Short link
https://repository.rudn.ru/en/records/article/record/4550/
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Chemistry of Heterocyclic Compounds. Латвийский институт органического синтеза Латвийской академии наук / Springer New York Consultants Bureau. Vol. 51. 2015. P. 639-646