A novel tandem cyclization of condensed 2,3-dialkynylpyrazines into [1,2,3]triazolo[1′,5′;1,2]pyrido[3,4-b]pyrazines promoted by sodium azide

被引：18

作者：

Gulevskaya, A. V. ^{[1
]}

Van Dang, Shee ^{[1
]}

Tyaglivy, A. S. ^{[1
]}

Pozharskii, A. F. ^{[1
]}

Kazheva, O. N. ^{[2
]}

Chekhlov, A. N. ^{[2
]}

Dyachenko, O. A. ^{[2
]}

机构：

[1] So Fed Univ, Dept Chem, Rostov Na Donu 344090, Russia

[2] Russian Acad Sci, Inst Problems Chem Phys, Chernogolovka 142432, Moscow Region, Russia

来源：

TETRAHEDRON | 2010年 / 66卷 / 01期

关键词：

ANIONIC CYCLOAROMATIZATION; HETEROCYCLIZATIONS; NEOCARZINOSTATIN; PATHWAY; ANALOGS;

D O I：

10.1016/j.tet.2009.11.039

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

6,7-Dialkynyl-1,3-dimethylpteridine-2,4(1H,3H)-diones and 2,3-dialkynylquinoxalines have been shown to react with sodium azide in DMF at room temperature giving rise 9,11-dimethyl- [1,2,3]triazolo[1',5';1,2]pyrido[4,3-g]pteridine-8,10(9H,11H)-diones and [1,2,3]triazolol[1',5';1,2]pyrido[3,4-b]quinoxalines. A novel tandem cyclization involves 1,3-dipolar cycloaddition of an azide ion to the carbon-carbon triple bond followed by intramolecular nucleophilic addition of the intermediate 1,2,3-triazole N-anion to another C C bond. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：146 / 151

页数：6

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GIRI, VS
DAS, SK
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KEIFER, P
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (04) : 767 - 769
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VALLS, N
SEGARRA, VM
BONJOCH, J
[J]. MAGNETIC RESONANCE IN CHEMISTRY, 1991, 29 (10) : 985 - 992
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[5] Synthesis of imidazo[1′,5′:1,2]pyrido [3,4-b]indole derivatives
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Palkó, M
Martinek, T
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[7] NEW PYRIMIDO[1',6'/1,2]PYRIDO[3,4-B]INDOLES
DOMANY, G
SZANTAY, C
BIHARI, M
SCHON, I
[J]. SYNTHETIC COMMUNICATIONS, 1993, 23 (13) : 1787 - 1794
[8] A novel approach to [1,2,3]triazolo[1,5-a]pyrazines
Jug, T
Polak, M
Trcek, T
Vercek, B
[J]. HETEROCYCLES, 2002, 56 (1-2) : 353 - 360
[9] SYNTHESIS OF 3-CARBOETHOXY-4-OXO-4H-PYRIMIDO[1',2'-1,5][1,2,4]TRIAZOLO[3,4-B]BENZOXAZOLE AND 5H-PYRIDO[3'',2''-5',6']PYRIMIDO[1',2'-1,5][1,2,4]-TRIAZOLO[3,4-B]BENZOXAZOLE-5-ONE - NOVEL HETEROCYCLES
RAMALINGAM, T
MURTY, MSR
SATTUR, PB
[J]. HETEROCYCLES, 1989, 29 (05) : 925 - 928
[10] Chemistry of furazano[3,4-b]pyrazine. 6. 1,2,3-triazolo[4,5-b]furazano[3,4-b]pyrazines
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[J]. Chemistry of Heterocyclic Compounds, 1998, 34 (9) : 1081 - 1085

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