878-02-4Relevant academic research and scientific papers
Cascade Ring-Opening Dual Halogenation of Cyclopropenones with Saturated Oxygen Heterocycles
Gao, Wen-Xia,Huang, Xiao-Bo,Liu, Miao-Chang,Miao, Wei-Hang,Wu, Hua-Yue,Zhou, Yun-Bing
, p. 9425 - 9430 (2021/12/14)
Represented is a CuX2- or I2-promoted ring-opening dual halogenation of cyclopropenones with saturated oxygen heterocycles, providing an efficient method for the synthesis of 3-haloacrylates. The ring-opening reaction enables the construction of two C–X (X = Cl, Br, or I) bonds and a C–O bond as well as the cleavage of two C–O bonds and a C–C bond in a single step. This protocol is highly atom economical, has an excellent substrate scope, and exhibits the ability for gram-scale reaction.
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.
