Selective N-Monoalkylation of 6-Aminouracils with Alcohols: An Environmentally Benign Protocol for the Synthesis of 6-Alkylaminouracils
A highly selective N-alkylation of 6-aminouracils with alcohols was achieved through the borrowing hydrogen approach using iridium catalysis. 6-Aminouracils and alcohols reacted in the presence of [Cp*IrI2]2 to give 6-monoalkyluracils selectively and in high yield (up to 99 %), usually in short reaction times (2 h). These results provide a new, green, and efficient protocol for the synthesis of 6-alkylaminouracils, which are very important intermediates for the synthesis of biologically active molecules.
Putra, Anggi Eka,Oe, Yohei,Ohta, Tetsuo
p. 392 - 397
(2018/01/27)
Study on the synthesis of 6-alkylaminouridines via the nucleophilic aromatic substitution reaction of 6-cyanouridine derivatives
6-Cyanouracil derivatives underwent direct substitution reactions with selective primary amines in the presence of N,N-dimethylaminopyridine as a catalyst to give the corresponding 6-alkylaminouracils. This reaction provides a facile access to versatile 6
Chemical models and their mechanistic implications for the transformation of 6-cyanouridine 5′-monophosphate catalyzed by orotidine 5′-monophosphate decarboxylase
The reactions of 6-cyano-1,3-dimethyluracil have been studied as chemical models to illustrate the mechanism for the transformation of 6-cyanouridine 5′-monophosphate (6-CN-UMP) to barbiturate ribonucleoside 5′-monophosphate (BMP) catalyzed by orotidine 5′-monophosphate decarboxylase (ODCase). The results suggest that the Asp residue in the ODCase active site plays the role of a general base in the transformation.