54507-99-2Relevant articles and documents
Palladium and Lewis-Acid-Catalyzed Intramolecular Aminocyanation of Alkenes: Scope, Mechanism, and Stereoselective Alkene Difunctionalizations
Pan, Zhongda,Wang, Shengyang,Brethorst, Jason T.,Douglas, Christopher J.
, p. 3331 - 3338 (2018/03/13)
An expansion of methodologies aimed at the formation of versatile organonitriles, via the intramolecular aminocyanation of unactivated alkenes, is herein reported. Importantly, the need for a rigid tether in these reactions has been obviated. The ease-of-synthesis and viability of substrates bearing flexible backbones has permitted for diastereoselective variants as well. We demonstrated the utility of this methodology with the formation of pyrrolidones, piperidinones, isoindolinones, and sultams. Furthermore, subsequent transformation of these motifs into medicinally relevant molecules is also demonstrated. A double crossover 13C-labeling experiment is consistent with a fully intramolecular cyclization mechanism. Deuterium labeling experiments support a mechanism involving syn-addition across the alkene.
Copper-catalyzed one-pot synthesis of unsymmetrical arylurea derivatives via tandem reaction of diaryliodonium salts with N -arylcyanamide
Li, Pengfei,Cheng, Guolin,Zhang, Hong,Xu, Xianxiang,Gao, Jingyuan,Cui, Xiuling
, p. 8156 - 8162 (2015/03/18)
An efficient "one-pot" approach to multiple substituted ureas from N-arylcyanamide and diaryliodonium salts has been presented. The two-step procedure involved the weak base-promoted chemoselective arylation of secondary amines with diaryliodonium and Cu-catalyzed nucleophilic addition of N-arylcyanamide with second diaryliodonium. The diverse unsymmetrical arylureas were obtained in up to 91% yield for 29 examples.
Iron(III) catalysed synthesis of unsymmetrical di and trisubstituted ureas - A variation of classical Ritter reaction
Basavaprabhu, Hosamani,Sureshbabu, Vommina V.
supporting information; experimental part, p. 2528 - 2533 (2012/04/23)
An application of the classical Ritter reaction for the synthesis of unsymmetrical di and trisubstituted ureas catalyzed by FeCl3 is described. The protocol is of significant interest in view of the easy availability of precursors, mild reaction conditions employed and interestingly its applicability for the alkylation of alcohols capable of forming stable carbocationic intermediates even to the sterically hindered moieties. The Royal Society of Chemistry 2012.
