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Pyridines from azabicyclo[3.2.0]hept-2-en-4-ones through a proposed azacyclopentadienone

Hemming, Karl, Khan, Musharraf, Kondakal, Vishnu, Rice, Craig R., Pitard, Arnaud and Qamar, Muhammad Ilyas (2012) Pyridines from azabicyclo[3.2.0]hept-2-en-4-ones through a proposed azacyclopentadienone. Organic Letters, 14 (1). pp. 126-129. ISSN 15237060

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    Abstract

    Pyridines have been formed by heating azabicyclo[3.2.0]hept-2-en-4-ones in toluene. The generation of a 3-azacyclopentadienone intermediate via a [2+2]-cycloreversion is proposed as the key step. A Diels-Alder reaction of a styrene, extrusion of carbon monoxide and loss of hydrogen then gives the pyridine. The process parallels the well-known synthesis of benzenes from cyclopentadienones. The azabicyclo[3.2.0]hept-2-en-4-ones were synthesized from the reaction between readily available cyclopropenones and 1-azetines, in which the cyclopropenones behave as all-carbon 1,3-dipolar equivalents.

    Item Type: Article
    Additional Information: Reprinted with permission from Org. Lett., 2012, 14 (1), pp 126–129 DOI: 10.1021/ol202924s Publication Date (Web): December 21, 2011 Copyright © 2011 American Chemical Society
    Subjects: Q Science > QD Chemistry
    Schools: School of Applied Sciences
    Related URLs:
    Depositing User: Karl Hemming
    Date Deposited: 12 Jan 2012 09:50
    Last Modified: 12 Jan 2012 09:56
    URI: http://eprints.hud.ac.uk/id/eprint/12491

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