Chemotherapeutical Agents, V. Syntheses and Activities of Novel Pyrimidines Derived from 5-Cyano-6-aryl-2-thiouracil

✍ Scribed by Ram, Vishnu J. ;Vanden Berghe, Dirk A. ;Vlietinck, Arnold J.

• Publisher: John Wiley and Sons
• Year: 1987
• Tongue: English
• Weight: 475 KB
• Volume: 1987
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.198719870831

✦ Synopsis

Tlic Scyano-6-aryl-2-thiourHciIs la-d were prepared '-3 for the syntheses of several other pyrimidine derivatives. In basic medium 1x1 reacted with picryl chloride yielding the unexpected benzothiazolo-pyrimidine 2. Heating a mixture of i and t.2dibromoctbanc in DMF in basic medium gave the thiazolopyrimidines 3a. d, while chc reaction of 1 with 1.3dibromopropane and 1.3-dibromo-2-propanol under similar conditions yielded the pyrimido-thiazine 3 b, c, e. Alkylation of 1 with alkyl ldides in alkaline medium in 1 : 2 and 1 : 1 ratios gave the diand monoaikyl dcrivatjves 4 and 5, respectiveIy. With hydrazine hydrate. 4s yielded the 2-hydrazi~opyrimidine 6 which cyclized to give the triazolo-pyrimidine 7 on refluxing in formic acid Similar reaction conditions were maintained for attempts to cydize 6 with acetic and propionic acid, but always the acylhydrazino derivatives 8a, b were isolated. Reaction of 6 with methyl 2cyano-3,3-bis(metbylthio)ate ' C15/871