ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The 5-cyano-6-aryl-2-thiouracils 1a-d were prepared1,2) for the syntheses of several other pyrimidine derivatives. In basic medium 1a reacted with picryl chloride yielding the unexpected benzothiazolo-pyrimidine 2. Heating a mixture of 1 and 1,2-dibromoethane in DMF in basic medium gave the thiazolopyrimidines 3a, d, while the reaction of 1 with 1,3-dibromopropane and 1,3-dibromo-2-propanol under similar conditions yielded the pyrimido-thiazine 3b, c, e. Alkylation of 1 with alkyl halides in alkaline medium in 1:2 and 1:1 ratios gave the di- and monoalkyl derivatives 4 and 5, respectively. With hydrazine hydrate, 4a yielded the 2-hydrazinopyrimidine 6 which cyclized to give the triazolo-pyrimidine 7 on refluxing in formic acid. Similar reaction conditions were maintained for attempts to cyclize 6 with acetic and propionic acid, but always the acylhydrazino derivatives 8a, b were isolated. Reaction of 6 with methyl 2-cyano-3,3-bis(methylthio)acrylate or with acetylacetone yielded the pyrazolo-pyrimidines 9 and 10, respectively. All products were screened for their potential fungicidal, bactericidal, and antiviral activities since several related compounds were shown to possess antimicrobial activities in a primary screening.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198719870831
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