197635-71-5

Upstream product

• 83196-21-8 N-(4-methoxybenzyl)-N’-phenylurea 
• 70978-37-9 1-(azidomethyl)-4-methoxybenzene 
• 103-71-9 phenyl isocyanate 

Downstream Products

• 1056476-69-7 ethyl 2-benzyl-2-(N-(4-methoxybenzylcarbamoyl)-N-(phenyl)carbamoyl)butanoate 
• 1394001-85-4 (E)-1-(4-methoxybenzyl)-5-(2-methylbenzylidene)-3-phenyldihydropyrimidine-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

Multicomponent Approach to Libraries of Substituted Dihydroorotic Acid Amides

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.

Three-component sequential synthesis of N,N′-disubstituted 5-arylidenedihydropyrimidine-2,4-dione

A three-component sequential process consisting in (1) in situ formation of carbodiimides by Staudinger reaction, (2) reaction with 2-(bromomethyl)-3-aryl- 2-propenoic acids, and (3) final cyclization of the resulting N-acylurea intermediates in order to obtain the synthesis of an array of N,N′-disubstituted 5-arylidenedihydropyrimidine-2,4-dione under mild conditions is presented.

Multicomponent, one-pot sequential synthesis of 1,3,5- and 1,3,5,5-substituted barbiturates

(Chemical Equation Presented) Carbodiimides and malonic acid monoethylesters readily react to afford N-acylurea derivatives that could be cyclized in situ by addition of a suitable base. This process represents a general and straightforward one-pot sequential synthesis of 1,3,5-trisubstituted barbiturates in very mild conditions (organic solvent/2 N NaOH aqueous solution, 20°C). Performing the reaction in the presence of an electrophile resulted in the formation of fully substituted (namely, 1,3,5,5- tetrasubstituted) barbiturates through a three-component one-pot sequential process. The latter, however, occurred only with highly reactive electrophiles, such as benzyl and, in some instances, allyl halides. In order to expand the scope of the process, we sought to develop a general method for the C-alkylation of 1,3,5-trisubstituted barbiturates. We found that C-alkylation occurred upon treatment of 1,3,5-trisubstituted barbiturates with an alkyl halide in CH 3CN at 120°C in the presence of anhydrous K2CO 3 affording the target 1,3,5,5-tetrasubstituted barbiturates in good yields. The multicomponent process was accomplished by combining the three steps in a one-pot sequential fashion, i.e., the condensation of carbodiimides with malonic acid monoethylesters, the cyclization of the resulting N-acylureas, and the C-alkylation of the resulting 1,3,5-substituted barbiturates. A detailed study of the influence of the structure of the reactants on the reaction outcome and mechanism is presented. By selective N′-deprotection of 1,3,5,5-tetrasubstituted barbiturates, the corresponding 1,5,5-trisubstituted barbiturates were also prepared.

Preparation of N,N'-bis(aryl)guanidines from electron deficient amines via masked carbodiimides

Preparation of N,N'-bis(aryl)guanidines by alkylation of electron deficient amines with trityl protected carbodiimides is described. Also reported is a method for the dehydration of N-trityl-N'-aryl ureas to the corresponding carbodiimides using the Burge