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

共 50 条

[11] 1,2,5-THIADIAZOLO[3,4-B]PYRAZINES
TONG, YC
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1975, 12 (03) : 451 - 453
[12] OXAZOLO[3',2'1,2]PYRIDO[3,4-B]INDOLES AND [1,3]-OXAZINO[3',2'1,2]-PYRIDO[3,4-B]INDOLES BY A SIMPLE CONDENSATION REACTION OF 3,4-DIHYDRO-BETA-CARBOLINE WITH ALPHA-HYDROXYCARBOXYLIC AND BETA-HYDROXYCARBOXYLIC ACIDS
WANNER, KT
WEBER, U
SYNTHESIS-STUTTGART, 1994, (04): : 387 - 390
[13] Chemistry of furazano[3,4-b]pyrazine.: 6.: 1,2,3-triazolo[4,5-e]furazano[3,4-b] pyrazines
Starchenkov, IB
Andrianov, VG
Mishnev, AF
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1998, (09): : 1259 - 1264
[14] First Synthesis of the Novel Triazolo[3,4-b][1,3,4]Thiadiazoles and Triazolo[3,4-b][1,3,4]Thiadiazines Linked Chromeno[2,3-b]Pyridine
Ibrahim, Magdy A. A.
Al-Harbi, Sami A. A.
Allehyani, Esam S. S.
Alqurashi, Esam A. A.
Alshareef, F. M.
POLYCYCLIC AROMATIC COMPOUNDS, 2024, 44 (01) : 361 - 374
[15] Synthesis and antiviral activity of novel [1,2,4]triazolo[3,4b][1,3,4]thiadiazoles, [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazepines
Farghaly, Abdel-Rahman
De Clercq, Erik
El-Kashef, Hussein
ARKIVOC, 2006, : 137 - 151
[16] SYNTHESIS AND PROPERTIES OF 1,2,4-TRIAZOLO[4,3-D]-1,2,4-TRIAZOLO[3,4-F]FURAZANO[3,4-B]PYRAZINES
KHISAMUTDINOV, GK
KOROLEV, VL
PARKHOMENKO, TN
SHARONOVA, VM
ARTEMEVA, ES
ABDRAKHMANOV, IS
SMIRNOV, SP
UGRAK, BI
RUSSIAN CHEMICAL BULLETIN, 1993, 42 (10) : 1700 - 1702
[17] Chemistry of furazano[3,4-b]pyrazines .2. Nucleophilic substitution of azide group in furazano[3,4-b]pyrazines
Andrianov, VG
Starchenkov, IB
Mishnev, AF
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1997, (08): : 1120 - 1124
[18] Oxygen-Rich 1,2,4-Triazolo[3,4-d]-1,2,4-triazolo[3,4-f]furazano[3,4-b]pyrazines as Energetic Materials
Sheremetev, Aleksei B.
Korolev, Vecheslav L.
Potemkin, Aleksandr A.
Aleksandrova, Natali S.
Palysaeva, Nadezhda V.
Hoang, Trung H.
Sinditskii, Valery P.
Suponitsky, Kyrill Yu.
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (11) : 1388 - 1397
[19] Synthesis of [1,2,3]triazolo[1,5-α][1,2,4]triazolo[5,1-c]pyrazines
Trcek, T
Vercek, B
ARKIVOC, 2003, : 246 - 252
[20] Studies on pyrazines .33. Synthesis of 2,3-diaminopyrazines via [1,2,5]thiadiazolo-[3,4-b]pyrazines
Sato, N
Mizuno, H
JOURNAL OF CHEMICAL RESEARCH-S, 1997, (07): : 250 - 251

← 1 2 3 4 5 →