13335-23-4Relevant academic research and scientific papers
Palladium-Catalyzed One-Pot Synthesis of N -Sulfonyl, N -Phosphoryl, and N -Acyl Guanidines
Qiao, Guanyu,Zhang, Zhen,Huang, Baoliang,Zhu, Liu,Xiao, Fan,Zhang, Zhenhua
, p. 330 - 340 (2018)
An efficient palladium-catalyzed cascade reaction of azides with isonitrile and amines is presented; it offers an alternative facile approach toward N -sulfonyl-, N -phosphoryl-, and N -acyl-functionalized guanidines in excellent yield. These series of substituted guanidines exhibit potential biological and pharmacological activities. In addition, the less reactive intermediate benzoyl carbodiimide could be isolated by silica gel column flash chromatography in moderate yield.
Tandem Coupling of Azide with Isonitrile and Boronic Acid: Facile Access to Functionalized Amidines
Zhang, Zhen,Huang, Baoliang,Qiao, Guanyu,Zhu, Liu,Xiao, Fan,Chen, Feng,Fu, Bin,Zhang, Zhenhua
supporting information, p. 4320 - 4323 (2017/04/04)
Amidine is a notable nitrogen-containing structural motif found in bioactive natural products and pharmaceuticals. Herein, a novel rhodium(I)-catalyzed tandem reaction of readily accessible azides with isonitriles and boronic acids via a carbodiimide intermediate is achieved. This protocol offers an alternative approach toward N-sulfonyl-, N-acyl-, and N- phosphoryl-functionalized, as well as general N-aryl and N-alkyl amidines with broad substrate scope. In addition, functionalized guanidines can also been synthesized when amines are used instead. The accomplishment of estrone-derived amidine and glibenclamide bioisosteres further reveals the practical utility of this strategy.
β-diketiminato nickel imides in catalytic nitrene transfer to isocyanides
Wiese, Stefan,Aguila, Mae Joanne B.,Kogut, Elzbieta,Warren, Timothy H.
, p. 2300 - 2308 (2013/06/27)
The β-diketiminato nickel(I) species [Me3NN]Ni(2-picoline) (1) serves as an efficient catalyst for carbodiimide (RN=C=NR′) formation in the reactions of a range of organoazides N3R with isocyanides R′NC. [Me3NN]Ni(CNR)2 (R = tBu, Ar (Ar = 2,6-Me2C6H3)) species provide carbodiimides RN=C=NAr′ upon reaction with Ar′N3 (Ar′ = 3,5-Me2C6H3). Nitrene transfer takes place via the intermediacy of nickel imides. Reaction of [MexNN]Ni(2-picoline) (x = 2 or 3) with Ar′N3 gives the new dinickel imides {[Me xNN]Ni}2(μ-NAr′) (4 (x = 3) and 5 (x = 2)) as deep purple, diamagnetic substances. The X-ray structure of {[Me 2NN]Ni}2(μ-NAr′) (5) features short Ni-N imide distances of 1.747(2) and 1.755(2) A along with a short Ni-Ni distance of 2.7210(3) A. These dinickel imides 4 and 5 react stoichiometrically with tBuNC to provide the corresponding carbodiimides tBuN=C=NAr′ in good yield. Azide transfer takes place upon reaction of 1 with TMS-N3 to give the square planar nickel(II) azide [Me3NN]Ni(N3)(2-picoline) (7). Stoichiometric reaction of dinickel dicarbonyl {[Me3NN]Ni} 2(μ-CO)2 with organoazides such as Ar′N 3 is sluggish, indicating that 1 is not an efficient catalyst for nitrene transfer from organoazides to CO to form isocyanates RN=C=O.
