53344-27-7Relevant academic research and scientific papers
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.
supporting information; experimental part, p. 126 - 129 (2012/02/16)
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.
GENERAL SYNTHESIS OF CYCLOPROPENONES AND THEIR ACETALS
Isaka, Masahiko,Ejiri, Satoshi,Nakamura, Eiichi
, p. 2045 - 2058 (2007/10/02)
Metalated cyclopropenone acetals 5 react with a variety of electrophiles, including alkyl halides, carbonyl compounds, vinyl iodides, vinyl triflates, and aryl iodides, to give substituted cyclopropenone acetals in high yield.Hydrolysis of the acetal unde
