299456-72-7Relevant articles and documents
Access to pyrrolo[2,1-: A] isoindolediones from oxime acetates and ninhydrin via Cu(i)-mediated domino annulations
Upare, Atul,Chouhan, Neeraj Kumar,Ramaraju, Andhavaram,Sridhar, Balasubramanian,Bathula, Surendar Reddy
, p. 1743 - 1746 (2020/03/17)
A copper-mediated domino condensation reaction of readily accessible oxime acetates with ninhydrin is reported to afford pyrrolo[2,1-a]isoindolediones via new C-C & C-N bond formations. A wide range of oxime acetates were shown to generally participate in the reaction to produce the condensed products in excellent yields. The necessary control experiments were performed and the mechanism is proposed to involve sequentially the formation of iminium radical via Cu-mediated N-O bond cleavage of oxime acetates, addition of the radical to ninhydrin and rearrangement via ring expansion.
Copper(0)/PPh3-Mediated Bisheteroannulations of o-Nitroalkynes with Methylketoximes Accessing Pyrazo-Fused Pseudoindoxyls
Meng, Huanxin,Xu, Zhenhua,Qu, Zhonghua,Huang, Huawen,Deng, Guo-Jun
supporting information, p. 6117 - 6121 (2020/08/12)
A copper(0)/PPh3-mediated cascade bisheteroannulation reaction of o-nitroalkynes with methylketoximes has been developed that provides viable access to a diverse range of pyrazo-fused pseudoindoxyl compounds. Synthetically useful functional groups including sensitive C-I bonds are compatible with this system. Mechanistic studies suggest a reaction cascade involving sequential PPh3-mediated deoxygenative cycloisomerization and copper-catalyzed [3 + 2] pyrazo-annulation.
Direct access to bis-S-heterocycles via copper-catalyzed three component tandem cyclization using S8 as a sulfur source
Zhou, Peiqi,Huang, Yubing,Wu, Wanqing,Yu, Wentao,Li, Jianxiao,Zhu, Zhongzhi,Jiang, Huanfeng
, p. 3424 - 3432 (2019/04/01)
A novel strategy for constructing sulfur containing bis-S-heterocyclic compounds from oxime esters/vinyl azide, phenylacetylene/aldehydes and elemental sulfur (S8) has been developed. These transformations show good functional group tolerance. Various bis-S-heterocyclic products were efficiently synthesized from easily prepared or widely commercially available starting materials. In this protocol, S8 successfully served as a two-sulfur atom donor for thiophene and thiazole rings, respectively.