Pyridines from Azabicyclo[3.2.0]hept-2-en-4-ones through a Proposed Azacyclopentadienone

Karl Hemming, Musharraf N. Khan, Vishnu V.R. Kondakal, Arnaud Pitard, M. Ilyas Qamar, Craig R. Rice

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)126-129
Number of pages4
JournalOrganic Letters
Issue number1
Early online date21 Dec 2011
Publication statusPublished - 6 Jan 2012


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