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
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TRANSFORMATIONS OF 4-ARYLPYRROLO[1,2-A][1,4]BENZODIAZEPINES IN THREE-COMPONENT REACTIONS WITH ACTIVATED ALKYNES AND CH, NH, SH, AND OH ACIDS

Article
Voskressensky L.G., Borisova T.N., Babakhanova M.I., Chervyakova T.M., Titov A.A., Novikov R.A., Toze F., Dang T.T.A., Varlamov A.V.
Chemistry of Heterocyclic Compounds. Латвийский институт органического синтеза Латвийской академии наук / Springer New York Consultants Bureau. Vol. 51. 2015. P. 639-646