Reduction and diazotization of ethyl 7-amino-3-tert-butyl-4-oxo-4,6-dihydropyrazolo[5,1-c][1,2,4]triazine-8-carboxylate

Autor:	Sergey M. Ivanov, L. M. Mironovich, A. O. Chizhov, E. D. Daeva
Rok vydání:	2017
Předmět:	010405 organic chemistry Organic Chemistry Ether Azo coupling 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound Acetic anhydride chemistry Ethyl acetoacetate Sodium azide Organic chemistry Carboxylate Azide Triazine
Zdroj:	Russian Journal of Organic Chemistry. 53:577-581
ISSN:	1608-3393 1070-4280
DOI:	10.1134/s1070428017040133
Popis:	The ester group in ethyl 7-amino-3-tert-butyl-4-oxo-4,6-dihydropyrazolo[5,1-c][1,2,4]triazine-8-carboxylate was converted for the first time to methyl by the action of lithium tetrahydridoborate in the presence of boron trifluoride–diethyl ether complex. This reaction has almost no analogies among other classes of organic compounds. New difficultly accessible 7-chloro and 7-azido derivatives were synthesized via diazotization of the reduction product, and treatment of the latter with acetic anhydride afforded the exhaustively acetylated derivative. Diazotization of ethyl 7-amino-3-tert-butyl-4-oxo-4,6-dihydropyrazolo-[5,1-c][1,2,4]triazine-8-carboxylate, followed by reaction with sodium azide, gave the corresponding azide, and the product of azo coupling with ethyl acetoacetate failed to undergo intramolecular cyclization to tricyclic pyrazolo[3,2-c: 5,1-c′]bis[1,2,4]triazine system.
Databáze:	OpenAIRE
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