The first example of an intramolecular Diels-Alder furan (IMDAF) reaction of iminium salts and its application in a short and simple synthesis of the isoindolo[1, 2-a]isoquinoline core of the jamtine and hirsutine alkaloids

1-(2-Furyl)-3, 4-dihydroisoquinolines, easily prepared from readily available phenethylamines undergo tandem alkylation/[4+2]-cycloaddition with allyl halides. The reaction proceeds via 2-allyl-1-furyl-3, 4- dihydroisoquinolinium salt formation and subsequent intramolecular exo-Diels-Alder reaction of furan with the allyl fragment (IMDAF reaction). The adducts formed include the basic structural element of the isoindolo[1, 2-a]isoquinoline alkaloids jamtine and hirsutine. © 2010 Elsevier Ltd. All rights reserved.

Authors
Zubkov F.I. 1 , Ershova J.D. 1 , Zaytsev V.P. 1 , Obushak M.D.2 , Matiychuk V.S.2 , Sokolova E.A. 1 , Khrustalev V.N.3 , Varlamov A.V. 1
Journal
Tetrahedron Letters
Publisher
Elsevier Ltd
Number of issue
52
Language
English
Pages
6822-6824
Status
Published
Link
External link
DOI
10.1016/j.tetlet.2010.10.046
Volume
51
Year
2010
Organizations
  • 1 Organic Chemistry Department, 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 Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., Moscow 119991, Russian Federation
Keywords
Alkaloids jamtine; Hirsutine; IMDAF; Intramolecular Diels-Alder furan reaction; Isoindolo[1,2-a]isoquinoline
Date of creation
19.10.2018
Date of change
13.08.2021
Short link
https://repository.rudn.ru/en/records/article/record/2633/
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