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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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.
|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|
|Depositing User:||Karl Hemming|
|Date Deposited:||12 Jan 2012 09:50|
|Last Modified:||12 Jan 2012 09:56|
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