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Tetrahedron LettersVolume 56, Issue 23, 17 November 2015, Article number 45521, Pages 3147-3150

The Rügheimer-Burrows reaction revisited: Facile preparation of 4-alkylisoquinolines and 3,5-dialkylpyridines from (partially) saturated amines(Article)(Open Access)

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  • aDepartment of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, NJ 08854, United States
  • bDepartment of Organic Synthesis Technology, Ural Federal University, Yekaterinburg, 620002, Russian Federation

Abstract

Abstract A long-known class of cyclic amine/aldehyde condensation reactions was reinvestigated. Benzoic acid was found to efficiently promote condensations of amines such as piperidine or 1,2,3,4-tetrahydroisoquinoline with aromatic aldehydes, resulting in amine β-functionalization and aromatization. These redox-neutral transformations provide 3,5-dialkylpyridines and 4-alkylisoquinolines in moderate to good yields, following short reaction times under microwave conditions. © 2015 Published by Elsevier Ltd.

Author keywords

Azomethine ylidesHeterocyclesRedox-neutral

Funding details

Funding sponsor Funding number Acronym
National Institutes of Health
See opportunities by NIH		NIH
National Institute of General Medical Sciences
See opportunities by NIGMS		R01GM101389-01NIGMS
Ural Federal UniversityUrFU

  • 1

    Financial support from the NIH−NIGMS (Grant R01GM101389-01 ) is gratefully acknowledged. A.Y.P. gratefully acknowledges financial support from the Ural Federal University (Support by Act 211 Government of the Russian Federation No. 02.A03.21.0006) and grant RFBR 14-03-31944 mol_a.

  • ISSN: 00404039
  • CODEN: TELEA
  • Source Type: Journal
  • Original language: English
  • DOI: 10.1016/j.tetlet.2014.11.137
  • Document Type: Article
  • Publisher: Elsevier Ltd

  Seidel, D.; Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, NJ, United States
© Copyright 2016 Elsevier B.V., All rights reserved.

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