Regioselective synthesis of 6-benzylthiazolo[3,2-b]1,2,4-triazoles during sonogashira coupling

被引：74

作者：

Heravi, MM ^{[1
]}

Kivanloo, A

Rahimzadeh, M

Bakavoli, M

Ghassemzadeh, M

Neumüller, B

机构：

[1] Alzahra Univ, Sch Sci, Dept Chem, Tehran 1993891167, Iran

[2] Ferdowsi Univ Mashhad, Sch Sci, Dept Chem, Mashhad 1331418, Iran

[3] Chem & Chem Engn Res Ctr Iran, Tehran 14335186, Iran

[4] Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 10期

关键词：

sonogashira coupling; thiazoles; triazoles; Pd-catalyzed reaction; thiazolotriazoles;

D O I：

10.1016/j.tetlet.2005.01.091

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 3-merciptopropargyl-1,2,4-ti-iazoles with various iodobenzenes catalyzed by Pd-Cu leads to the regioselective formation of 6-beiizyltliiazolo[3,2-b]1,2,4-triazoles 4. The structure of 4d was confirmed by X-ray analysis. (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1607 / 1610

页数：4

共 25 条

[1]

[Anonymous], 2015, Acta Crystallogr., V71, P3

[2]

Bates DK, 1999, HETEROCYCLES, V51, P475

[3] Palladium-catalyzed heteroannulation leading to heterocyclic structures with two heteroatoms:: A highly convenient and facile method for a totally regio- and stereoselective synthesis of (Z)-2,3-dihydro-2-(ylidene)-1,4-benzo- and -naphtho[2,3-b]dioxins [J].

Chowdhury, C ;

Chaudhuri, G ;

Guha, S ;

Mukherjee, AK ;

Kundu, NG .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) :1863-1871

[4]

Dale DJ, 2001, J CHEM SOC P1, V1, P424

[5] SYNTHESIS AND BIOLOGICAL-ACTIVITIES OF SOME 3,6-DISUBSTITUTED THIAZOLO[3,2-B][1,2,4]TRIAZOLES [J].

EROL, DD ;

CALIS, U ;

DEMIRDAMAR, R ;

YULUG, N ;

ERTAN, M .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1995, 84 (04) :462-465

[6] Pd-Cu catalyzed heterocyclization during Sonogashira coupling:: synthesis of 3-benzylthiazolo[3,2-a]benzimidazole [J].

Heravi, MM ;

Keivanloo, A ;

Rahimizadeh, M ;

Bakavoli, M ;

Ghassemzadeh, M .

TETRAHEDRON LETTERS, 2004, 45 (29) :5747-5749

[7] Heteroannulation through palladium catalysis: A novel cyclization leading to regioselective synthesis of 3-substituted thiazolo[3,2-C]1,2,4-triazin-5-ones [J].

Heravi, MM ;

Kivanloo, A ;

Rahimizadeh, M ;

Bakavoli, M ;

Ghassemzadeh, M .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2002, 177 (10) :2491-2496

[8]

Heravi MM, 1997, MONATSH CHEM, V128, P1143, DOI 10.1007/BF00807564

[9]

Heravi MM, 1995, J CHEM RES-S, P480

[10] Sodium hydroxide:: a mild and inexpensive catalyst for the regioselective synthesis of 2-substituted 5-methylthiazolo[3,2-b]-s-triazoles [J].

Heravi, MM ;

Tajbakhsh, M .

JOURNAL OF CHEMICAL RESEARCH, 1998, (08) :488-489

← 1 2 3 →