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 journalArticle

28 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)126-129
Number of pages4
JournalOrganic Letters
Volume14
Issue number1
Early online date21 Dec 2011
DOIs
Publication statusPublished - 6 Jan 2012

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Pyridines
Azetines
pyridines
Diels-Alder reactions
Styrene
Cycloaddition Reaction
Toluene
Carbon Monoxide
Benzene
styrenes
Heating
carbon monoxide
Extrusion
toluene
Hydrogen
Carbon
benzene
heating
carbon
hydrogen

Cite this

Hemming, Karl ; Khan, Musharraf N. ; Kondakal, Vishnu V.R. ; Pitard, Arnaud ; Qamar, M. Ilyas ; Rice, Craig R. / Pyridines from Azabicyclo[3.2.0]hept-2-en-4-ones through a Proposed Azacyclopentadienone. In: Organic Letters. 2012 ; Vol. 14, No. 1. pp. 126-129.
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Pyridines from Azabicyclo[3.2.0]hept-2-en-4-ones through a Proposed Azacyclopentadienone. / Hemming, Karl; Khan, Musharraf N.; Kondakal, Vishnu V.R.; Pitard, Arnaud; Qamar, M. Ilyas; Rice, Craig R.

In: Organic Letters, Vol. 14, No. 1, 06.01.2012, p. 126-129.

Research output: Contribution to journalArticle

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