39531-32-3Relevant academic research and scientific papers
P(III)-Assisted Electrochemical Access to Ureas via in situ Generation of Isocyanates from Hydroxamic Acids
Meng, Haiwen,Sun, Kunhui,Xu, Zhimin,Tian, Lifang,Wang, Yahui
supporting information, p. 1768 - 1772 (2021/03/26)
An external oxidant-free protocol for the generation of isocyanates from hydroxamic acids assisted by trivalent phosphine under mild electrochemical conditions was reported. The process started with the anodic oxidation of hydroxamic acids, followed by reacting with phosphine to form corresponding alkoxyphosphoniums and subsequent rearrangement with the release of tri-substituted phosphine oxide as the driving force to give isocyanates, which were trapped by N-based nucleophiles to produce various ureas. This method provides a broadly applicable procedure to access isocyanate intermediates under mild electrochemical conditions.
Efficient Direct Halogenation of Unsymmetrical N -Benzyl- and N -Phenylureas with Trihaloisocyanuric Acids
Sanabria, Carlos M.,Costa, Bruno B. S.,Viana, Gil M.,De Aguiar, Lúcia C. S.,De Mattos, Marcio C. S.
, p. 1359 - 1367 (2017/12/26)
A simple and efficient methodology for the direct halogenation of N -phenylureas was developed using trihaloisocyanuric acids in acetonitrile at room temperature. This protocol proved to be effective for the construction of N -phenylureas with different patterns of substitution. Additionally, less reactive N -benzylureas were halogenated in the presence of a mixture of trifluoroacetic acid and acetonitrile at room temperature.
An easy access to unsymmetrical ureas: A photocatalytic approach to the Lossen rearrangement
Yadav, Arvind K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
, p. 24498 - 24503 (2014/07/07)
An efficient and operationally simple method for the synthesis of unsymmetrical ureas from various hydroxamic acids and amines has been developed. Plausibly, the protocol involves visible-light-initiated in situ formation of Vilsmeier-Haack reagent and COBr2 with CBr4 and a catalytic amount of DMF in the presence of Ru(bpy)3Cl2 as a photocatalyst to bring about the Lossen rearrangement at room temperature. the Partner Organisations 2014.
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.
New and simple synthesis of acid azides, ureas and carbamates from carboxylic acids: Application of peptide coupling agents EDC and HBTU
Sureshbabu, Vommina V.,Lalithamba,Narendra,Hemantha
experimental part, p. 835 - 840 (2010/06/20)
Conversion of carboxylic acids into acid azides using peptide coupling agents, EDC and HBTU is described. The procedure is efficient, practical and applicable to a diverse range of carboxylic acids including N-protected amino acids. Using the same reagents, one-pot synthesis of ureas, dipeptidyl urea esters and carbamates from acids has also been achieved. The Royal Society of Chemistry 2010.
α-Haloalkyl Haloformates and Related Compounds 3.1 A Facile Synthesis of Symmetrical and Unsymmetrical Ureas via Chloromethyl Carbamates
Patonay, Tamas,Patonay-Peli, Erzsebet,Zolnai, Laszlo,Mogyorodi, Ferenc
, p. 4253 - 4265 (2007/10/03)
Chloromethyl carbamates were prepared by the reaction of chloromethyl chloroformates with amines and found to produce mono-, symmetrically or unsymmetrically di- and trisubstituted ureas including their N-hydroxy and N-alkoxy derivatives in moderate to good yield.
β-Tosylethylamine: A Useful Reagent for Preparation of N-Protected Amides, Carbamates, and Related Compounds. Application to Synthesis of β-Lactams
DiPietro, Darren,Borzilleri, Robert M.,Weinreb, Steven M.
, p. 5856 - 5857 (2007/10/02)
Readily prepared β-tosylethylamine (3) can be used to synthesize N-tosylethyl (TSE)-protected amido compounds and β-lactams, which can be deprotected under mild conditions with potassium tert-butoxide.
Syntheses of novel bicyclic β-lactams by intramolecular nucleophile transfer reactions of N-tosyloxy β-lactams
Guzzo,Teng,Miller
, p. 8275 - 8292 (2007/10/02)
Intramolecular nucleophile transfer reaction of several N-tosyloxy β- lactams was applied to construct a new six-membered ring in the product bicyclic β-lactams. The bicyclic products generally possessed cis stereochemistry on the β-lactam ring. The major
