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Reduction and Diazotization of Ethyl 7-Amino-3-tert-butyl-4-oxo-4,6-dihydropyrazolo[5,1-c][1,2,4]triazine-8-carboxylate
被引:9
作者:
Mironovich, L. M.
[1
]
Ivanov, S. M.
[2
]
Chizhov, A. O.
[2
]
Daeva, E. D.
[2
]
机构:
[1] Southwest State Univ, Ul 50 Let Oktyabrya 94, Kursk 305040, Russia
[2] Russian Acad Sci, Zelinskii Inst Organ Chem, Leninskii Pr 47, Moscow 119991, Russia
关键词:
REACTIVITY;
DIBORANE;
D O I:
10.1134/S1070428017040133
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
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.
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页码:577 / 581
页数:5
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