54507-99-2Relevant academic research and scientific papers
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.
supporting information, 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.
A novel one-pot synthesis of isothiocyanates and cyanamides from dithiocarbamate salts using environmentally benign reagent tetrapropylammonium tribromide
Kuotsu, Neivotsonuo Bernadette,Jamir, Latonglila,Phucho, Tovishe,Sinha, Upasana Bora
, p. 832 - 841 (2018/01/17)
A highly efficient and simple protocol for the synthesis of isothiocyanates and cyanamides from their respective amines in the presence of a mild, efficient, and non-toxic reagent tetrapropylammonium tribromide is described. High environmental acceptability of the reagents, cost effectiveness and high yields are the important attributes of this methodology.
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.
An efficient transformation of ethers to N,N′-disubstituted ureas in a Ritter type reaction
Panduranga, Veladi,Basavaprabhu,Sureshbabu, Vommina V.
, p. 975 - 979 (2013/04/10)
A simple, mild, and an alternative protocol for the preparation of N,N′-disubstituted ureas from readily available ethers and cyanamides as starting materials is described. The protocol explores the reactivity of ether in a Ritter type reaction with cyanamide in the presence of BF 3·Et2O and resulting in the formation of N,N′-disubstituted urea. Divinyl ether as well as MTBE (methyl tert-butyl ether) can be employed as ether components to afford allyl and tert-butyl ureas respectively.
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.
Bromineless bromine as an efficient desulfurizing agent for the preparation of cyanamides and 2-aminothiazoles from dithiocarbamate salts
Yella, Ramesh,Kavala, Veerababurao,Patel, Bhisma K.
, p. 792 - 805 (2011/04/22)
In a one-pot procedure, bromineless brominating reagent 1,1'-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) has been used as a desulfurizing agent in the preparation of organic cyanamides and substituted thiazoles starting from dithiocarbamic acid salts. In this approach, alkyl/aryl isothiocyantes were first obtained by the desulfurization of dithiocarbamic acid salts with EDPBT. The in situ-generated isothiocyanates reacts with an aqueous ammonia, forming alkyl or aryl thioureas, which on subsequent oxidative desulfurization with EDPBT led to the formation of corresponding cyanamides in good yields. Alternatively, an efficient one-pot synthesis of substituted thiazoles has been achieved by the condensation of the in situ-generated 1-aryl thioureas with the in situ-generated -bromoketones from ketones, again using EDPBT. The reagent EDPBT can be easily prepared from the readily available reagents. Desulfurizing ability dominates over its brominating ability for substrates amenable to bromination.
Sodium bis(trimethylsilyl)amide in the 'one-flask' transformation of isocyanates to cyanamides
Wong, Fung Fuh,Chen, Chun-Yen,Yeh, Mou-Yung
, p. 559 - 562 (2007/10/03)
Cyanamides were successfully prepared in a 'one-flask' reaction from isocyanates by use of sodium bis(trimethylsilyl)amide as the deoxygenating agents in THF at room temperature. Georg Thieme Verlag Stuttgart.
