61700-60-5Relevant academic research and scientific papers
SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)
Ding, Chengrong,Ge, Shuting,Wei, Junjie,Zhang, Guofu,Zhao, Yiyong
, p. 17288 - 17292 (2020/05/18)
A simple, mild and practical cascade process for the direct conversion of aldehydes to cyanamides was developed featuring a wide substrate scope and great functional group tolerability. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable cyanamides in a pot, atom, and step-economical manner with a green nitrogen source. This protocol will serve as a robust tool for the installation of the cyanamide moiety in various complicated molecules.
A cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO2F2-activated Tiemann rearrangement
Zhang, Guofu,Zhao, Yiyong,Ding, Chengrong
, p. 7684 - 7688 (2019/08/30)
A simple, mild and practical process for the direct conversion of nitriles to cyanamides was newly discovered and exhibited a wide substrate scope as well as great functional group-tolerability (36 examples). In this efficient strategy, the in situ generated amidoximes obtained from the reaction of nitriles with hydroxylamine subsequently underwent Tiemann rearrangement, producing the corresponding cyanamides with great isolated yields under SO2F2. Additionally, the control experiments reportedly shed light on the tentative mechanism involved in the formation and elimination of the key intermediate: a sulfonyl ester.
Selective Gold-Catalysed Synthesis of Cyanamides and 1-Substituted 1H-Tetrazol-5-Amines from Isocyanides
?koch, Karel,Císa?ová, Ivana,?těpni?ka, Petr
supporting information, p. 13788 - 13791 (2018/09/14)
The newly discovered gold-catalysed reaction of isocyanides with hydrazoic acid generated in situ from trimethylsilyl azide and methanol (or, alternatively, from NaN3/AcOH) produces either cyanamides or 1-substituted 1H-tetrazol-5-amines, depending on the amount of available HN3. The reaction proceeds selectively and in generally high yields of either product, thus providing a particularly convenient access to a wide range of substituted 1H-tetrazol-5-amines that are rather difficult to access otherwise.
One-Pot Synthesis of N-Monosubstituted Ureas from Nitriles via Tiemann Rearrangement
Wang, Chien-Hong,Hsieh, Tsung-Han,Lin, Chia-Chi,Yeh, Wen-Hsiung,Lin, Chih-An,Chien, Tun-Cheng
, p. 1823 - 1826 (2015/08/06)
Amidoximes, obtained from the reaction of nitriles with hydroxylamine, underwent Tiemann rearrangement in the presence of benzenesulfonyl chlorides (TsCl or o-NsCl) to form the N-substituted cyanamides. Subsequently, acidic hydrolysis of the cyanamides afforded the corresponding N-monosubstituted ureas. The synthesis of N-monosubstituted ureas from nitriles was accomplished by three steps in one pot, which provides a direct access to versatile N-monosubstituted urea derivatives from a wide variety of nitriles.
Practical synthesis of N -substituted cyanamides via tiemann rearrangement of amidoximes
Lin, Chia-Chi,Hsieh, Tsung-Han,Liao, Pen-Yuan,Liao, Zhen-Yuan,Chang, Chih-Wei,Shih, Yu-Chiao,Yeh, Wen-Hsiung,Chien, Tun-Cheng
, p. 892 - 895 (2014/03/21)
A facile and general synthesis of various N-substituted cyanamides was accomplished by the Tiemann rearrangement of amidoximes with benzenesulfonyl chlorides (TsCl or o-NsCl) and DIPEA.
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.
Synthesis of 2,1-benzisoxazoles by nucleophilic substitution of hydrogen in nitroarenes activated by the azole ring
Pokhodylo, Nazariy T.,Teslenko, Yuriy O.,Matiychuk, Vasyl S.,Obushak, Mykola D.
scheme or table, p. 2741 - 2748 (2010/02/28)
Reaction of 1-nitro-4-(1,2,3-triazolyl/tetrazolyl)benzenes with arylacetonitriles in an alcoholic medium in the presence of excess alkali gives novel 2,1-benzisoxazoles. These findings indicate a high reactivity of nitroarenes activated by the azole ring due to their electron-deficient character. Moreover, it was found that annulation of the isoxazole ring occurred regioselectively in disubstituted nitroarenes. In the case of 1-(4-nitrophenyl)-1H-tetrazole, the tetrazole ring cleaved faster than the sH-adduct was formed. Georg Thieme Verlag Stuttgart.
Desulfurization and transformation of isothiocyanates to cyanamides by using sodium bis(trimethylsilyl)amide
Chen, Chun-Yen,Wong, Fung Fuh,Huang, Jiann-Jyh,Lin, Shao-Kai,Yeh, Mou-Yung
supporting information; scheme or table, p. 6505 - 6507 (2009/04/06)
Sodium bis(trimethylsilyl)amide was first used as the desulfurizing agent for the conversion of isothiocyanates to cyanamides in a 'one-flask' reaction. Crown Copyright
15N NMR Chemical Shifts for Cyanamide, Phenylcyanamide and a Series of Phenyl-Substituted Derivatives
Buchanan, G. W.,Crutchley, R. J.
, p. 552 - 553 (2007/10/02)
15N NMR chemical shifts are reported for cyanamide, phenylcyanamide and nine substituted phenylcyanamide derivatives.Results are discussed in terms of the degree of the ? interaction between the cyanamide moiety and the aromatic ring and the stereoelectronic influence of the substituents. - Keywords: 15N NMR Cyanamide Phenylcyanamide
