3878-67-9Relevant academic research and scientific papers
Reaction of N-Phenyltrifluoromethanesulfonamide with Carbodiimides
Tolstikova,Danilevich, Yu. S.,Shainyan
, p. 395 - 398 (2019)
N-Phenyltrifluoromemanesulfonamide reacted with N,N′-dicyclohexylcarbodiimide in methylene chloride to give exchange products, N-cyclohexyltrifluoromethanesulfonamide and N-cyclohexyl-N′-phenylcarbodiimide. Reaction of the latter with trifluoromethanesulf
Ultrasound-assisted synthesis of substituted guanidines from thioureas
Pattarawarapan, Mookda,Jaita, Subin,Wangngae, Sirilak,Phakhodee, Wong
, p. 1354 - 1358 (2016)
Ultrasound-assisted synthesis of guanidine derivatives was developed using 2,4,6-trichloro-1,3,5-triazine as an inexpensive dehydrosulfurization reagent. Both 1,3-alkylaryl- and 1,3-diaryl-thioureas were rapidly converted into carbodiimides before subsequent reaction with aromatic or aliphatic amines. The method allows rapid access to highly substituted guanidines in good to excellent yields under mild conditions and with minimal use of solvent.
Copper(II)-Catalyzed Aerobic Oxidative Desulfitative 6π Electrocyclization: Efficient Synthesis of Diverse 4-Aminoquinolines
Shi, Lou,Pan, Ling,Li, Yifei,Liu, Qun
, p. 2457 - 2470 (2017)
The C?C bond formation via C?S bond activation (disclosed in 2000) has received increasing attention. However, stoichiometric amounts of exogenous thiophilic reagents are generally required as thiolate scavengers. Herein, a new model for the synthesis of 4-aminoquinolines, the copper(II)-catalyzed aerobic oxidative desulfitative 6π cyclization of the readily available N-arylimino ketene N,S-acetals is described. The reaction can proceed efficiently under mild conditions without any exogeneous thiolate scavengers (due to the formation of disulfide as the by-product) to afford diverse 4-aminoquinolines, a privileged structure motif displaying antimalarial activity, with a wide range of functional groups at the C-2 to C-8 positions. (Figure presented.).
Electrochemical Synthesis of Carbodiimides via Metal/Oxidant-Free Oxidative Cross-Coupling of Amines and Isocyanides
Badsara, Satpal Singh,Jaiswal, Pradeep K.,Malviya, Bhanwar Kumar,Sharma, Siddharth,Verma, Ved Prakash
supporting information, (2020/03/19)
This work discloses an electrochemical oxidative cross-coupling of amines with aryl and aliphatic isocyanides. In an undivided cell, the reaction proceeds without involving any transition-metal catalyst, oxidant, or toxic reagents providing carbodiimides in good yields, thereby circumventing stoichiometric chemical oxidants, with H2 as the only byproduct. Moreover, carbodiimides were in situ converted into unsymmetrical ureas in moderate to good yields using an electricity ON-OFF strategy.
Ultrasonic-assisted synthesis of carbodiimides from N,N′-disubstituted thioureas and ureas
Duangkamol, Chuthamat,Pattarawarapan, Mookda,Phakhodee, Wong
, p. 1945 - 1949 (2016/10/21)
A facile and efficient sonochemical method for the preparation of carbodiimides from their corresponding thioureas or ureas was described. Using Ph3P–I2 combination in the presence of triethylamine, various diaryl, aryl–alkyl, as well as dialkyl substituted substrates could be converted into carbodiimides in good-to-excellent yields within short reaction times under mild conditions with simple experimental setup. Graphical abstract: [Figure not available: see fulltext.]
Palladium-catalyzed cross-coupling reaction of azides with isocyanides
Zhang, Zhen,Li, Zongyang,Fu, Bin,Zhang, Zhenhua
supporting information, p. 16312 - 16315 (2015/11/16)
An efficient palladium-catalyzed cross-coupling reaction of azides with isocyanides is developed, providing a general synthetic route to unsymmetric carbodiimides with excellent yields. This method shows a broad substrate scope, including not only aryl azides, but also unactivated benzyl and alkyl azides. Furthermore, from readily available substrates, Pd-catalyzed coupling with a tandem amine insertion cascade to obtain unsymmetric trisubstituted guanidines has been achieved in a one-pot fashion.
Synthesis of phosphaguanidines by hydrophosphination of carbodiimides with phosphine boranes
Busacca, Carl A.,Milligan, John A.,Rattanangkool, Eakkaphon,Ramavarapu, Cyrus,Chen, Anji,Saha, Anjan K.,Li, Zhibin,Lee, Heewon,Geib, Steven J.,Wang, Guijun,Senanayake, Chris H.,Wipf, Peter
, p. 9878 - 9887 (2015/01/09)
The direct addition of anionic secondary phosphine boranes to carbodiimides yields both chiral and achiral phosphaguanidine boranes under ambient temperature conditions. An analogous preparation of menthol-derived phosphinite boranes is also described. These products can be deborinated to give the corresponding phosphines, and subsequently oxidized to give phosphine oxides. The robustness of this method was further demonstrated in the synthesis of structurally novel cyclic phosphaguanidines. (Chemical Equation Presented).
Multi-component synthesis of peptide-sugar conjugates
Bellucci, Maria Cristina,Terraneo, Giancarlo,Volonterio, Alessandro
, p. 2421 - 2444 (2013/06/05)
Recent years have witnessed a growing interest in the development of new methods for linking sugars to peptides or proteins because natural glycopeptides or neoglycoconjugates with well defined chemical structures are very important tools to study diverse biological phenomena. Herein we report a novel, one-pot, three-component process for the synthesis of peptide-urea conjugates incorporating a hexafluorovaline or an aspartic acid alkyl ester residue under very mild conditions and high yields. The reaction has been exploited for the synthesis of a wide array of structurally diverse peptide-sugar conjugates through a regiospecific four-component, one-pot sequential domino process, by generating the reacting sugar-carbodiimides in situ from readily accessible starting materials. The Royal Society of Chemistry 2013.
A New synthetic protocol for the preparation of carbodiimides using a hypervalent iodine(III) reagent
Zhu, Chenjie,Xu, Dan,Wei, Yunyang
supporting information; experimental part, p. 711 - 714 (2011/04/24)
A new, simple, and efficient preparation of symmetrical and unsymmetrical carbodiimides from the corresponding thioureas via dehydrosulfurization using a hypervalent iodine(III) reagent is described. The oxidation afforded carbodiimides in excellent yields and high selectivity. A possible mechanism for the transformation is proposed. Georg Thieme Verlag Stuttgart New York.
