7597-73-1Relevant articles and documents
Practical bromination of arylhydroxylamines with SOBr2 towards ortho-bromo-anilides
Du, Yuanbo,Feng, Lei,Gao, Hongyin,Guo, Lirong,Lu, Haifeng,Xi, Zhenguo
supporting information, (2021/05/19)
A facile approach for synthesizing ortho-bromoanilides from readily available aryhydroxylamines and thionyl bromide is demonstrated in this work. Mild reaction conditions and broad scope of substrates ranging from heterocyclic structures to pharmaceutics-potential motifs are used in the reactions of this paper. Efficient bromination of ortho C–H bonds of the aryhydroxylamines has been achieved. Ortho-bromoanilide products were obtained in good to excellent yields, and model scaled-up reactions of this synthetic approach are shown in this work.
A Simple Synthesis of Phenanthrene
Allen, Robert W.,Gilbertson, Jeffrey J.,Gribble, Gordon W.
, (2020/03/30)
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Synthesis of polycyclic aminocyclobutane systems by the rearrangement of N-(ortho-Vinylphenyl) 2-Azabicyclo[3.1.0]hexane derivatives
Wasilewska, Agnieszka,Wozniak, Bartosz A.,Doridot, Gabriel,Piotrowska, Kamila,Witkowska, Natalia,Retailleau, Pascal,Six, Yvan
supporting information, p. 11759 - 11767 (2013/09/12)
The acid-catalysed thermal rearrangements of a family of N-aryl 2-azabicyclo[3.1.0]hexanes is described. These substrates, designed in such a way that the aromatic system is conjugated with an alkene group located at the ortho position relative to the nitrogen atom, have been prepared by using an intramolecular Kulinkovich-de Meijere reaction. The rearrangements can then be conducted either under standard thermal conditions or with microwave activation. Depending on the conditions applied and the substitution pattern, dihydroquinoline or polycyclic aminocyclobutane derivatives can be obtained. A mechanistic discussion is provided, with the proposition of the initial protonation of the aminocyclopropane moiety to give an iminium intermediate. By analogy with related intermolecular reactions, the involvement of electrocyclic reactions among the series of elementary steps that follow is put forward. Small rings: The acid-catalysed rearrangement of bicyclic N-aryl aminocyclopropanes with an alkene group located at the ortho position, either under standard thermal conditions or with microwave activation, is described (see scheme). The method provides access to dihydroquinoline and polycyclic aminocyclobutane derivatives. By analogy with related intermolecular reactions, the involvement of an electrocyclic reaction is proposed. Copyright