ISSN:
1434-4475
Keywords:
5-Dialkylamino-2-aryl-1,2,3-triazoles
;
4-Amino-2,6-dioxo-tetrahydropyrid-3-yl-pyridiniumchloride
;
2-Arylhydrazono-2-cyan-N-chloracetylacetamide
;
Arylhydrazono-2-cyan-N,N-dialkylacetamidines
;
Arylhydrazonomalononitriles
;
4-Imino-5-arylazo-6-dialkylamino-1,4-dihydropyrimidines
;
13C-NMR
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Summary The title compounds3 were synthesized by reaction of arlyhydrazono-malononitriles1 with secondary amines and used for subsequent cyclization reactions. Thus,3 undergoes cyclooxidation by treatment with CuSO4/pyridine to form the 5-dialkylamino-2-aryl-1,2,3-triazolo-4-carbonitriles4. From4 a and hydrazine hydrate/DMF the 4-(1,3,4-triazolyl-5)-1,2,3-triazole5 c is obtainable. The chloroacetylation of3 is accompanied by hydrolysis of the amino group to yield the arylhydrazono-N-chloracetyl cyanoacetamides6. The quaternisation of6 with pyridins is followed by the Thorpe cyclization to form the 4-amino-5-arylazo-6-hydroxy-3-pyridinio-pyrid-2-on-chlorides8, useful as cationic dyes. The reaction of3 with trichloroacetonitriles yields the 5-arylazo-4-imino-2-trichlormethyl-1,4-dihydropyrimidines10 a–c which can be converted into the 5-arylazo-2-hydrazino-pyrimidine derivatives10 d–f. From10 d the 6-phenylazo-triazolo[4,3-a]pyrimidine derivative11 is obtainable. From3 and phenylisothiocyanate the 5-arylazo-4-imino-1,4-dihydropyrimidin-2-thiones12 arise. The structures were investigated by13C-NMR-spectroscopy.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00809365
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