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
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.

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