A Stereocontrolled 1,2-Addition Reaction of Tetrazoles with Alkyl Propiolates for the Synthesis of Highly Functionalized Enamines

被引：16

作者：

Luo, Kai ^{[1
]}

Meng, Lingguo ^{[2
]}

Zhang, Yicheng ^{[2
]}

Zhang, Xiuli ^{[1
,3
]}

Wang, Lei ^{[2
,3
]}

机构：

[1] Anhui Agr Univ, Dept Chem, Hefei 230036, Anhui, Peoples R China

[2] Huaibei Normal Univ, Dept Chem, Huaibei 235000, Anhui, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 04期

基金：

美国国家科学基金会;

关键词：

1; 2-addition reaction; alkyl propiolates; N-cyano enamines; silver catalysis; tetrazoles; CATALYZED REACTIONS; SILVER; DERIVATIVES; EFFICIENT; CYCLOISOMERIZATION; REARRANGEMENT; ISOQUINOLINES; ALKYNOATES; IMINES;

D O I：

10.1002/adsc.201200868

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A stereocontrolled 1,2-addition reaction of 1-aryl-1H-tetrazoles with alkyl propiolates for the synthesis of highly functionalized enamines was developed. In the presence of silver oxide (Ag2O), the 1,2-addition reaction generated (Z)-N-cyano enamines in good yields with exclusive formation of the Z-isomers. Meanwhile, the 1,2-addition reaction generated (E)-N-cyano enamines in the presence of Ag2O and potassium carbonate (K2CO3) with high stereoselectivity and yields.

引用

页码：765 / 780

页数：16

共 50 条

[1] Silver-mediated synthesis of heterocycles [J].

Alvarez-Corral, Miriam ;

Munoz-Dorado, Manuel ;

Rodirguez-Garcia, Ignacio .

CHEMICAL REVIEWS, 2008, 108 (08) :3174-3198

[2] Building Heterocyclic Systems with RC(OR)2+ Carbocations in Recyclable Bronsted Acidic Ionic Liquids: Facile Synthesis of 1-Substituted 1H-1,2,3,4-Tetrazoles, Benzazoles and Other Ring Systems with CH(OEt)3 and EtC(OEt)3 in [EtNH3][NO3] and [PMIM(SO3H)][OTf] [J].

Aridoss, Gopalakrishnan ;

Laali, Kenneth K. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (15) :2827-2835

[3] CYTOSTATIC TETRAZOLE-BUTENOLIDE CONJUGATES: LINKING TETRAZOLE AND BUTENOLIDE RINGS VIA STILLE COUPLING AND BIOLOGICAL ACTIVITY OF THE TARGET SUBSTANCES [J].

Balsanek, Vojtech ;

Tichotova, Lucie ;

Kunes, Jiri ;

Spulak, Marcel ;

Pour, Milan ;

Votruba, Ivan ;

Buchta, Vladimir .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2009, 74 (7-8) :1161-1178

[4] Enantioselective organocatalysis using SOMO activation [J].

Beeson, Teresa D. ;

Mastracchio, Anthony ;

Hong, Jun-Bae ;

Ashton, Kate ;

MacMillan, David W. C. .

SCIENCE, 2007, 316 (5824) :582-585

[5] Nitrile Imines: Matrix Isolation, IR Spectra, Structures, and Rearrangement to Carbodiimides [J].

Begue, Didier ;

Qiao, Greg GuangHua ;

Wentrup, Curt .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (11) :5339-5350

[6] Silver(I)-Catalyzed Dual Activation of Propargylic Alcohol and Aziridine/Azetidine: Triggering Ring-Opening and Endo-Selective Ring-Closing in a Cascade [J].

Bera, Milan ;

Roy, Sujit .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22) :8814-8817

[7] Silver(I)-Catalyzed Cascade: Direct Access to Furans from Alkynyloxiranes [J].

Blanc, Aurelien ;

Tenbrink, Katharina ;

Weibel, Jean-Marc ;

Pale, Patrick .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (11) :4360-4363

[8]

Brown M., 1967, U. S. Patent, Patent No. [3,338,915, 3338915]

[9]

Cook A.G., 1988, ENAMINESSYNTHESIS ST, V2nd, P717, DOI [10.1201/9780203758014, DOI 10.1201/9780203758014]

[10] A novel synthesis of 1-aryl tetrazoles promoted by employing the synergy of the combined use of DMSO and an ionic liquid as the solvent system at ambient temperature [J].

Dighe, Satish N. ;

Jain, Kishor S. ;

Srinivasan, Kumar V. .

TETRAHEDRON LETTERS, 2009, 50 (45) :6139-6142

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