1205-86-3Relevant academic research and scientific papers
Gram Scalable Method to Synthesize Biscarbodiimides and Asymmetric Monocarbodiimides: A Platform to Access an Array of Phosphaguanidines, Amidines, and Guanidines
Bailey, Brad,Camelio, Andrew M.,Davis, Anna,Krasovskiy, Arkady
, (2021/11/12)
A mild, broadly functional group tolerant methodology has been developed to access a variety of mono- and bis-carbodiimides in good yield and high purity on multigram scale. Direct addition into these versatile motifs facilitated the rapid synthesis of a library of novel amidinines, guanidines, and phosphaguandines.
Pos [...] 4 group metal olefin polymerization catalyst
-
, (2019/08/27)
Embodiments are directed to phosphaguanidine metal complexes of formula I and using those complexes in α-olefin polymerization systems.
Multicomponent Approach to Libraries of Substituted Dihydroorotic Acid Amides
Bellucci, Maria Cristina,Sacchetti, Alessandro,Volonterio, Alessandro
supporting information, p. 705 - 715 (2019/10/02)
A process featuring a sequential multicomponent reaction followed by a regioselective postcyclization strategy was implemented for the facile synthesis of N,N′-disubstituted dihydroorotic acid amides under mild conditions. We obtained, for the first time, a library of 29 derivatives, encompassing 19 Nα-substituted-N4-dihydroorotyl-4-aminophenylalanine derivatives, a key residue of gonadotropin-releasing hormone antagonist Degarelix. The corresponding products were prepared from easily accessible starting materials in good to excellent yields with broad substrate scope.
Nitrene Metathesis and Catalytic Nitrene Transfer Promoted by Niobium Bis(imido) Complexes
Kriegel, Benjamin M.,Bergman, Robert G.,Arnold, John
supporting information, p. 52 - 55 (2016/01/25)
We report a metathesis reaction in which a nitrene fragment from an isocyanide ligand is exchanged with a nitrene fragment of an imido ligand in a series of niobium bis(imido) complexes. One of these bis(imido) complexes also promotes nitrene transfer to catalytically generate asymmetric dialkylcarbodiimides from azides and isocyanides in a process involving the Nb(V)/Nb(III) redox couple.
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 N-glycosyl conjugates through a multicomponent domino process
Bellucci, Maria Cristina,Volonterio, Alessandro
, p. 2386 - 2397 (2014/04/17)
The development of efficient methods for the combinatorial synthesis of N-glycosyl conjugates is vital for many fields of modern synthetic organic chemistry. Herein, we report a multicomponent domino process for the regioselective synthesis of a large array N-glycosyl-Asp-urea conjugates, which could be further functionalized in a chemoselective way, starting from easily accessible reactants such as N-glycosylamines, fumaric acid monoesters, azides, and isocyanates. The process occurs under very mild conditions, does not require the use of strong bases/acids or high temperature, and is highly versatile, working efficiently with a range of protecting groups and substituents.
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.
Regioselective multicomponent sequential synthesis of hydantoins
Olimpieri, Francesca,Bellucci, Maria Cristina,Marcelli, Tommaso,Volonterio, Alessandro
, p. 9538 - 9555 (2013/01/16)
The development of new practical and green methods for the synthesis of small heterocycles is an attractive area of research due to the well-known potential of heterocyclic small molecule scaffolds in the drug discovery process. Herein we report a one-pot, three-component sequential procedure for the synthesis of diversely 1,3,5- and 1,3,5,5-substituted hydantoins, in high yields and very mild conditions, using readily accessible starting materials such as azides, iso(thio)cyanates and substituted α-halo-acetic carboxylic acids. This methodology is especially convenient for the synthesis of spiro-hydantoins, which are particularly interesting bioactive compounds in medicinal chemistry. The Royal Society of Chemistry 2012.
The efficient synthesis of carbodiimides using a titanium imido complex
Anderson, James C.,Bou-Moreno, Rafael
experimental part, p. 9182 - 9186 (2011/01/12)
An efficient rt synthesis of carbodiimides or ureas from the combination of a titanium imido complex 2 and a range of 12 aryl and aliphatic isocyanates is described. Control experiments suggest that carbodimide formation is via heterocumulene metathesis t
A mild, efficient approach for the synthesis of 1,5-disubstituted hydantoins
Olimpieri, Francesca,Bellucci, Maria Cristina,Volonterio, Alessandro,Zanda, Mateo
scheme or table, p. 6179 - 6188 (2010/03/04)
An efficient and straightforward two-step procedure for the synthesis of N-1 alkyl/aryl-substituted hydantoins was developed, starting from easily available starting materials. The procedure envisages a highly reglospecific domino condensation/aza-Michael
