A synthesis of functionalized 2-imino-1,3-thiazoles from tetramethylguanidine, isothiocyanates, and 2-chloro-1,3-dicarbonyl compounds

被引：12

作者：

Yavari, Issa ^{[1
]}

Malekafzali, Alaleh ^{[1
]}

Seyfi, Samereh ^{[1
]}

机构：

[1] Tarbiat Modares Univ, Dept Chem, Tehran, Iran

来源：

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY | 2014年 / 11卷 / 02期

关键词：

2-Imino-1,3-thiazole; Tetramethylguanidine; Isothiocyanate; 2-Chloro-1,3-dicarbonyls; CHEMISTRY;

D O I：

10.1007/s13738-013-0299-0

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Hantzsch method for thiazole synthesis is modified via the reaction of 2-chloro-1,3-dicarbonyl compounds with 2-(amidosulfanylenemethyl)-1,1,3,3-tetramethylguanidines (prepared in situ from tetramethylguanidine and isothiocyanates), to afford functionalized 2-imino-1,3-thiazoles in good yields.

引用

收藏

页码：285 / 288

页数：4

相关论文

共 15 条

[1] Synthesis of 2-(o-hydroxyaryl)-4-arylthiazoles by regioselective Pd(0)-catalyzed cross-coupling [J].

Bach, T ;

Heuser, S .

TETRAHEDRON LETTERS, 2000, 41 (11) :1707-1710

[2]

Heck S, 2000, SYNLETT, P424

[3] TETRATHIAFULVALENES AS BUILDING-BLOCKS IN SUPRAMOLECULAR CHEMISTRY [J].

JORGENSEN, T ;

HANSEN, TK ;

BECHER, J .

CHEMICAL SOCIETY REVIEWS, 1994, 23 (01) :41-51

[4] Synthesis of 2-alkoxy-substituted thiophenes, 1,3-thiazoles, and related S-Heterocycles via Lawesson's reagent-mediated cyclization under microwave irradiation: Applications for liquid crystal synthesis [J].

Kiryanov, AA ;

Sampson, P ;

Seed, AJ .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7925-7929

[5]

LEHN JM, 1995, SUPRAMOL CHEM, pCH8

[6]

Metzger J.V., 1979, Thiazole and its Derivatives

[7] The synthesis and activity of oxazole and thiazole analogues of urocanic acid [J].

Millan, DS ;

Prager, RH ;

Brand, C ;

Hart, PH .

TETRAHEDRON, 2000, 56 (05) :811-816

[8] Intermolecular alkyl/aryl exchange of 2-iminothiazoles with isothiocyanates and isocyanates: scopes and limitations [J].

Shin, Dongyun ;

Lee, Jihoon ;

Hahn, Hoh-Gyu .

TETRAHEDRON, 2010, 66 (30) :5707-5713

[9] MULTICOMPONENT REACTIONS IN ORGANIC-CHEMISTRY [J].

UGI, I ;

DOMLING, A ;

HORL, W .

ENDEAVOUR, 1994, 18 (03) :115-122

[10] Synthesis and biological evaluation of novel bisheterocycle-containing compounds as potential anti-influenza virus agents [J].

Wang, WL ;

Yao, DY ;

Gu, M ;

Fan, MZ ;

Li, JY ;

Xing, YC ;

Nan, FJ .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (23) :5284-5287