Pyridinium salts-versatile reagents for the regioselective synthesis of functionalized thiazocino[2,3-b]indoles by tandem dinucleophilic reactions of thiooxindoles

被引：27

作者：

Kiamehr, Mostafa ^{[1
,2
]}

Moghaddam, Firouz Matloubi ^{[1
]}

Gormay, Pavel V. ^{[2
]}

Semeniuchenko, Volodymyr ^{[3
]}

Villinger, Alexander ^{[2
]}

Langer, Peter ^{[2
,4
]}

Iaroshenko, Viktor O. ^{[2
,3
]}

机构：

[1] Sharif Univ Technol, Dept Chem, Lab Organ Synth & Nat Prod, Tehran, Iran

[2] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[3] Natl Taras Shevchenko Univ, UA-01033 Kiev 33, Ukraine

[4] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany

来源：

TETRAHEDRON | 2012年 / 68卷 / 47期

关键词：

Condensation; Heterocycles; Nucleophilic addition; Pyridines; Regioselectivity; 1,3-BIS(SILYL ENOL ETHERS); BRIDGED INDOLE ALKALOIDS; N-ALKYLPYRIDINIUM SALTS; 1ST TOTAL-SYNTHESIS; 1,1-BIS(TRIMETHYLSILYLOXY)KETENE ACETALS; STEREOSELECTIVE-SYNTHESIS; 1-ACYLPYRIDINIUM SALTS; AKUAMMILINE ALKALOIDS; NUCLEOPHILIC-ADDITION; STRYCHNOS ALKALOIDS;

D O I：

10.1016/j.tet.2012.09.059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of thiooxindoles with various 2- and 3-substituted pyridinium salts afforded a variety of functionalized thiazocinoindoles. The products have been prepared in good to excellent yields by regioselective dinucleophilic C/S-cyclocondensation of thiooxindoles with pyridinium salts. (c) 2012 Elsevier Ltd. All rights reserved.

引用

页码：9685 / 9693

页数：9

共 36 条

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[2] An alternative approach to the synthesis of functionalized pyrido[2,3-b]indoles
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[3] Cyclization Routes for the Synthesis of Functionalized Pyrano[2,3-b]indolones, Pyrazolo[3,4-b]indoles, and Furo[2,3-b]indoles
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SYNTHESIS-STUTTGART, 2013, 45 (09): : 1235 - 1246
[4] Selective Synthesis of Polyfunctionalized Pyrido[2,3-b]indoles by Multicomponent Domino Reactions
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[5] Au-Catalyzed Synthesis of Thiopyrano[2,3-b]indoles Featuring Tandem Rearrangement and Hydroarylation
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[6] Regioselective Electrooxidative [3+2] Annulation between Indole and Aniline Derivatives to Construct Functionalized Indolo[2,3-b]indoles
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[7] Copper-catalyzed tandem arylation-cyclization of 2-alkynylaryl isothiocyanates with diaryliodonium salts: an efficient synthesis of thiochromeno[2,3-b] indoles
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[8] Synthesis of diversely functionalized hexahydropyrrolo[2,3-b]indoles using domino reactions, olefination, isomerization and Claisen rearrangement followed by reductive cyclization
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[10] Versatile synthesis of 2-functionalized dihydrothiazolo[2,3-b]quinazolines through regioselective electrophilic intramolecular heterocyclization of 3-alkenyl-2-thioxoquinazolin-4-ones
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