40886-81-5Relevant academic research and scientific papers
N-heterocyclic carbene catalyzed oxidative coupling of aldehydes with carbodiimides under aerobic conditions: Efficient synthesis of N-acylureas
Soeta, Takahiro,Tabatake, Yuhta,Fujinami, Shuhei,Ukaji, Yutaka
supporting information, p. 2088 - 2091 (2013/06/05)
The oxidative coupling reaction of aldehydes with N,N′-disubstituted carbodiimides catalyzed by N-heterocyclic carbenes under aerobic conditions has been achieved. This reaction gives the corresponding N-acylurea derivatives in good to high yields. Various kinds of aldehydes including aliphatic ones and carbodiimides are applicable to this reaction.
2-thiophenecarbohydrazides: A novel efficient method for the synthesis of 2-thiophenecarbohydrazide
Elshaarawy, Reda F.M.,Janiakb, Christoph
experimental part, p. 1202 - 1208 (2012/03/09)
Hydrazinolysis of carboxylic acid esters in alcoholic solutions is the standard method for preparing carbohydrazides (carboxylic hydrazides). Here we report an efficient process, involving the reaction of activated esters or amides with hydrazine, for the preparation of thiophenecarbohydrazides in yields larger than 90% and high purity. With this new method, a series of heteroaryl-, aryl-, or aralkyl- substituted carbohydrazides were synthesized and characterized. The X-ray crystal structure of 2-thiophenecarbohydrazide (thiophene-2-carboxylic hydrazide, 2-thenoyl-hydrazine) has revealed that it crystallizes in the monoclinic system, space group P21/c, with cell parameters of a = 6.1202(2), b = 8.3907(3), c = 12.5332(5) A, β = 98.6577(11)?, Z = 4, R(F) = 0.0455 and wR(F2) = 0.1805, T = 293 K.
Chemoselective alcoholysis of acylureas
Kishikawa,Eida,Kohmoto,Yamamoto,Yamada
, p. 173 - 175 (2007/10/02)
Two methods for the chemoselective alcoholysis of acylureas were developed to generate esters and amides, respectively. In alcoholysis using sodium methoxide in methanol, methoxide attacked the acyl carbonyl to give the corresponding methyl ester. While in alcoholysis using lithium benzyloxide in diethyl ether, benzyloxide attacked the urea carbonyl to give the amide. The chemoselectivity originates in the different chelating abilities of the metals and the polarity of the solvents.
