Synthesis and crystal structure characterization of two new antibacterial agents: 5-[1-(2,3- and 2,4-dichlorophenyl)-2-phenylethyl]-2,4,6-trichloropyrimidines

✍ Scribed by H. Allouchi; Y. Fellahi; C. Héabert; Y. Frangin; C. Courseille

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2003
• Tongue: English
• Weight: 75 KB
• Volume: 40
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570400106

✦ Synopsis

Abstract

The synthesis of 5‐[1‐(2,3‐dichlorophenyl)‐2‐phenylethyl]‐2,4,6‐trichloropyrimidine (4a) and 5‐[1‐(2,4‐dichlorophenyl)‐2‐phenylethyl]‐2,4,6‐trichloropyrimidine (4b) is described. These compounds were prepared by chlorination of the corresponding 5‐substituted barbituric acids obtained by treatment of the 5‐ben‐zylidenebarbituric acids with benzylzinc bromide in the preceding step. These new trichloropyrimidines belong to a series of pyrimidine derivatives which show in vitro antibacterial activity against the undesirable human bacterial flora of the axilla and foot. The characterization of these compounds were performed by spectroscopy and X‐ray structure determination. Compounds 4a and 4b crystallize in the monoclinic system. In the crystal of 4a there are two conformers A and B both of which are the same type of conformation, and are different from that found in the structure of 4b. The crystal cohesion results from numerous very week Van der Waals interactions.