Four-component reaction of cyclic amines, 2-aminobenzothiazole, aromatic aldehydes and acetylenedicarboxylate

被引：10

作者：

Gao, Hong ^{[1
]}

Sun, Jing ^{[1
]}

Yan, Chao-Guo ^{[1
]}

机构：

[1] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225002, Peoples R China

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 9卷

基金：

中国国家自然科学基金;

关键词：

benzothiazole; domino reaction; electron-deficient alkyne; multicomponent reaction; pyrrolidinone; QUINOLINE-DMAD ZWITTERION; MULTICOMPONENT SYNTHESIS; FACILE SYNTHESIS; DIALKYL ACETYLENEDICARBOXYLATES; 1,4-DIPOLAR CYCLOADDITION; 3-COMPONENT REACTION; EFFICIENT SYNTHESIS; METHYL PROPIOLATE; DOMINO REACTIONS; ARYLAMINES;

D O I：

10.3762/bjoc.9.330

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The four-component reaction of 2-aminobenzothiazole, aromatic aldehydes, acetylenedicarboxylate and piperidine or pyrrolidine in ethanol afforded the functionalized 2-pyrrolidinones containing both benzothiazolyl and piperidinyl (or pyrrolidinyl) units in good yields. On the other hand, the similar four-component reactions resulted in the functionalized morpholinium or piperidinium 2-pyrrolidinon-3-olates in the presence of p-toluenesulfonic acid.

引用

页码：2934 / 2939

页数：6

共 34 条

[1] [2+2] Cycloaddition of electron-poor acetylenes to (E)-3-dimethylamino-1-heteroaryl-prop-2-en-1-ones: synthesis of highly functionalized 1-heteroaroyl-1,3-butadienes [J].

Bezensek, Jure ;

Kolesa, Tanja ;

Groselj, Uros ;

Wagger, Jernej ;

Stare, Katarina ;

Meden, Anton ;

Svete, Jurij ;

Stanovnik, Branko .

TETRAHEDRON LETTERS, 2010, 51 (26) :3392-3397

[2] Concise assembly of highly substituted furan-fused 1,4-thiazepines and their Diels-Alder reactions with benzynes [J].

Ding, Hanfeng ;

Zhang, Yiping ;

Bian, Ming ;

Yao, Weijun ;

Ma, Cheng .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (02) :578-584

[3] Synthesis of functionalized 2-pyrrolidinones via domino reactions of arylamines, ethyl glyoxylate and acetylenedicarboxylates [J].

Gao, Hong ;

Sun, Jing ;

Yan, Chao-Guo .

TETRAHEDRON, 2013, 69 (02) :589-594

[4] Synthesis of the functionalized spiro[indoline-3,5′-pyrroline]-2,2′-diones via three-component reactions of arylamines, acetylenedicarboxylates, and isatins [J].

Han, Ying ;

Wu, Qun ;

Sun, Jing ;

Yan, Chao-Guo .

TETRAHEDRON, 2012, 68 (41) :8539-8544

[5] Efficient synthesis of pentasubstituted pyrroles via one-pot reactions of arylamines, acetylenedicarboxylates, and 3-phenacylideneoxindoles [J].

Han, Ying ;

Sun, Yan ;

Sun, Jing ;

Yan, Chao-Guo .

TETRAHEDRON, 2012, 68 (39) :8256-8260

[6]

HUISGEN R, 1968, Z CHEM, V8, P290

[7] 1.4-DIPOLARE CYCLOADDITIONEN .2. DREIKOMPONENTEN-REAKTIONEN DES ISOCHINOLINS MIT ACETYLENDICARBONSAUREESTER UND VERSCHIEDENEN DIPOLAROPHILEN [J].

HUISGEN, R ;

MORIKAWA, M ;

HERBIG, K ;

BRUNN, E .

CHEMISCHE BERICHTE-RECUEIL, 1967, 100 (04) :1094-&

[8] One-pot four-component domino reaction for the synthesis of substituted dihydro-2-oxypyrrole catalyzed by molecular iodine [J].

Khan, Abu T. ;

Ghosh, Arindam ;

Khan, Md. Musawwer .

TETRAHEDRON LETTERS, 2012, 53 (21) :2622-2626

[9]

Kielland N., 2010, Top. Heterocycl. Chem, V25, P127, DOI DOI 10.1007/7081_2010_42

[10] One-Pot Silver-Catalyzed and PIDA-Mediated Sequential Reactions: Synthesis of Polysubstituted Pyrroles Directly from Alkynoates and Amines [J].

Liu, Weibing ;

Jiang, Huanfeng ;

Huang, Liangbin .

ORGANIC LETTERS, 2010, 12 (02) :312-315

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