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Molecular Diversity

, Volume 9, Issue 1–3, pp 229–231 | Cite as

Microwave assisted IMDAF# reaction: Microwave irradiation applied with success to cycloaddition reaction of N-propargyl-N-p-tolyl-N-2-furfurylamines

  • Ana Dunja Mance
  • Krešimir Jakopčić
Full-length paper

Abstract

The new tertiary furfurylamine with triple bond as a dienophylic part i. e. N-(5-methyl-2-furfuryl)-N-prop-2-ynyl-p-toluidine (1) was prepared and the intramolecular Diels-Alder reaction of the amine (1) was performed under microwave irradiation conditions and by heating a benzene solution of the amine under nitrogen. Comparing the results of the usual thermal and the MAOS reaction, we confirmed our expectations that MAOS could promote the outcome of IMDA reaction of the suitably N-substituted tertiary 2-furfuryl-amines. In the present example, N-p-tolyl-5-methyl-5,7a-dihydro-5,7a-epoxyisoindoline was obtained in much better yield and of higher purity.

Keywords

alkynylarylfurfurylamine [4+2]cycloaddition epoxyisoindoline IMDAF# MAOS## 

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Copyright information

© Springer Science + Business Media, Inc. 2005

Authors and Affiliations

  1. 1.Faculty of Chemical Engineering and Technology, Department of Organic ChemistryUniversity of ZagrebMarulićev trg 20, ZagrebCroatia

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