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Die Acylierung von 5-Amino-1 H-1, 2, 4-triazolen. Eine 13C-NMR.-Studie

✍ Scribed by Tammo Winkler; Haukur Kristinsson

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
347 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

The Acylation of 5‐Amino‐1 H‐1,2,4‐triazoles. A ^13^C‐NMR. Study

The acylation of 3‐substituted‐5‐amino‐1 H‐1,2,4‐triazoles (1) with methyl chloroformate or dimethylcarbamoyl chloride yielded mainly 1‐acyl‐5‐amino‐1,2,4‐triazoles (2 and 3). Acylation of 3‐methyl‐, 3‐methoxy‐ and 3‐methylthio‐5‐amino‐1 H‐1,2,4‐triazole (1b, 1c and 1d) with methyl chloroformate gave up to 10% of the 1‐acyl‐3‐amino‐1,2,4‐triazoles. For the unsubstituted 5‐amino‐1,2,4‐triazole (1a), a (1:1)‐mixture of the 3‐ and 5‐isomers 2a and 4 was obtained in dioxane in the presence of triethylamine. No 4‐acylated product was detected in contrast to earlier reports. The structures of the reaction products were determined with the aid of proton coupled ^13^C‐NMR. spectra using the corresponding N‐methyl‐1,2,4‐triazoles as reference compounds.

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