Microwave‐Assisted N‐Nitroarylation of Some Pyrimidine and Purine Nucleobases.

Abstract

The efficient, clean, and rapid method proceeds via nucleophilic aromatic substitution and affords N 1 -nitroaryl pyrimidines and N 9 -nitroaryl purines regioselectively in reasonable yields. -(KHALAFI-NEZHAD*, A.; ZARE, A.; PARHAMI, A.; NAVID, M.; RAD, S.; NEJABAT, G. R.; Can. J. Chem. 84 (2006) 7, 979-985; Dep. Chem., Coll. Sci., Shiraz Univ., Shiraz 71454, Iran; Eng.) -Bartels 09-156

Microwave-promoted Facile and Efficient Preparation of N-(alkoxycarbonylmethyl) Nucleobases − Building Blocks for Peptide Nucleic Acids

“…It is worth mentioning that the same results were achieved when 2a was employed as the alkylating agent under the same conditions (entries 6-10). Substituting 5-H with CH 3 , Cl, or I only resulted in slight variations in yield, indicating that no obvious substitutent-effect existed [26]. Disappointingly, alkylation of 1e gave very poor results and only starting material was recovered.…”

“…The use of microwave-assisted organic syntheses has attracted considerable interest over the last two decades, leading to remarkable decreases in reaction times, significant enhancements of yields, easier workups and better regioselectivity [21][22][23][24][25][26][27][28][29]. Herein, we report a rapid, facile and practical protocol for the formation of N-(methoxycarbonylmethyl)-and N-(n-propoxycarbonylmethyl) nucleobases.…”