Cyclization of (1,2,4,5-tetrazin-3-yl)hydrazones to 3,7-dihydro-1,2,4-triazolo[4,3-b]-1,2,4,5-tetrazines

被引：8

作者：

Tolshchina, S. G. ^{[1
]}

Vyakhireva, A. G. ^{[1
]}

Ignatenko, N. K. ^{[1
]}

Ishmetova, R. I. ^{[1
]}

Ganebnykh, I. N. ^{[1
]}

Slepukhin, P. A. ^{[1
]}

Rusinov, G. L. ^{[1
]}

机构：

[1] Russian Acad Sci, Ural Branch, I Ya Postovsky Inst Organ Synth, 22-20 Ul S Kovalevskoi, Ekaterinburg 620041, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2009年 / 58卷 / 06期

基金：

俄罗斯基础研究基金会;

关键词：

3,7-dihydro-1,2,4-triazolo[4,3-b]-1,2,4,5-tetrazines; 3,6-disubstituted 1,2,4,5-tetrazines; hydrazones; cyclization; ring-chain isomerism; nucleophilic substitution; alkylation; SERIES;

D O I：

10.1007/s11172-009-0168-2

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The intramolecular cyclization of (6-R-1,2,4,5-tetrazin-3-yl)hydrazones of ketones (R is 3,5-dimethylpyrazol-1-yl, 4-methylimidazol-1-yl, or 2-alkylidenehydrazino) giving rise to the previously unknown 3,7-dihydro-1,2,4-triazolo[4,3-b]-1,2,4,5-tetrazines, including spiro compounds, was studied. The reactivity and the yields of the reaction products depend on the structure of the alkylidene fragment and the nature of the substituent in the tetrazine ring.

引用

页码：1281 / 1290

页数：10

共 11 条

[1] Synthesis of the bi-heterocyclic parent ring system 1,2,4-triazolo[4,3-b][1,2,4,5]tetrazine and some 3,6-disubstituted derivatives [J].

Chavez, DE ;

Hiskey, MA .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, 35 (06) :1329-1332

[2]

DAUNIS J, 1969, B SOC CHIM FR, P2492

[3]

GANEBNYKH IN, 2003, THESIS I ORGANIC SYN, P229

[4]

KITAEV YP, 1974, GIDRAZONY, P415

[5]

Latosh NI, 1999, ZH ORG KHIM+, V35, P1392

[6] Synthesis of 1,2,4,5-tetrazines, symmetrically and unsymmetrically 3,6-disuhstituted by N-nucleophiles [J].

Rusinov, G. L. ;

Latosh, N. I. ;

Ganebnykh, I. I. ;

Ishmetova, R. I. ;

Ignatenko, N. K. ;

Chupakhin, O. N. .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 42 (05) :757-765

[7]

Rusinov G. L., 1999, RUSS J ORG CHEM+, V35, P1350

[8]

Shawali AS, 2008, HETEROCYCLES, V75, P1479

[9] Annelated[1,2,4,5]tetrazines [J].

Shawali, AS ;

Elsheikh, SM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (03) :541-559

[10]

ZAHER HA, 1987, INDIAN J CHEM B, V26, P110

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