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：19

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

共 25 条

[1] ALKYNYL-QUINOXALINES AND DIALKYNYL-QUINOXALINES - SYNTHESIS OF CONDENSED QUINOXALINES [J].

AMES, DE ;

BROHI, MI .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (07) :1384-1389

[2] Chelation-controlled Bergman cyclization: Synthesis and reactivity of enediynyl ligands [J].

Basak, A ;

Mandal, S ;

Bag, SS .

CHEMICAL REVIEWS, 2003, 103 (10) :4077-4094

[3] REACTIONS OF 1,3-DIMETHYL-5,6-DIAMINOURACIL [J].

BLICKE, FF ;

GODT, HC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (10) :2798-2800

[4] Reaction of (Z)-1-aryl-3-hexen-1,5-diynes with sodium azide:: Synthesis of 1-aryl-1H-benzotriazoles [J].

Chen, ZY ;

Wu, MJ .

ORGANIC LETTERS, 2005, 7 (03) :475-477

[5]

Dang V. S., 2005, CHEM HETEROCYCL COMP, V41, P124

[6] Synthesis and heterocyclizations of 3-alkynyl-6,8-dimethylpyrimido-[4,5-c]pyridazine-5,7(6H,8H)-diones and their lumazine analogues [J].

Gulevskaya, AV ;

Van Dang, S ;

Pozharskii, AF .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 42 (03) :413-419

[7] Purines, pyrimidines, and related fused systems 20. Heterocyclizations of 6-alkynyl-1,3-dimethyllumazines. Synthesis of pyrrole and thiophene analogs of some natural pteridines [J].

Gulevskaya, AV ;

Van Shee, D ;

Pozharskii, AF .

RUSSIAN CHEMICAL BULLETIN, 2003, 52 (06) :1403-1410

[8]

HECKEL A, 1986, HELV CHIM ACTA, V69, P708

[9]

HEHHION GF, 1957, J AM CHEM SOC, V79, P2142

[10] PARA BENZYNE - GENERATION AS AN INTERMEDIATE IN A THERMAL ISOMERIZATION REACTION AND TRAPPING EVIDENCE FOR 1,4-BENZENEDIYL STRUCTURE [J].

JONES, RR ;

BERGMAN, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (02) :660-&

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