Synthesis of Novel bis-1,5-Disubstituted-1H-Tetrazoles by an Efficient Catalyst-Free Ugi-Azide Repetitive Process

被引：17

作者：

Cardenas-Galindo, Luis E. ^{[1
]}

Islas-Jacome, Alejandro ^{[2
]}

Colmenero-Martinez, Karla M. ^{[2
]}

Martinez-Richa, Antonio ^{[2
]}

Gamez-Montano, Rocio ^{[2
]}

机构：

[1] Univ Tecnol Salamanca, Dept Quim Area Ambiental, Salamanca 36750, Gto, Mexico

[2] Univ Guanajuato, Dept Quim, Div Ciencias Nat & Exactas, Guanajuato 36050, Gto, Mexico

来源：

MOLECULES | 2015年 / 20卷 / 01期

关键词：

bis-1,5-disubstituted-1H-tetrazoles; Ugi-azide repetitive reaction; MW-assisted synthesis; catalyst-free; chelating agents; BIOLOGICAL EVALUATION; TETRAZOLE;

D O I：

10.3390/molecules20011519

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A series of five novel bis-1,5-disubstituted-1H-tetrazoles (bis-1,5-DS-1H-T) were quickly prepared by a catalyst-free Ugi-azide repetitive process from easily accessible starting materials in excellent yields, either at room temperature (88%-95%) or using mild MW-heating conditions (80%-91%). These molecules may have a wide range of applications, such as chelating agents, organocatalysts and luminescent materials, and mainly as bioactive compounds.

引用

页码：1519 / 1526

页数：8

共 14 条

[1] Organic azides:: An exploding diversity of a unique class of compounds [J].

Bräse, S ;

Gil, C ;

Knepper, K ;

Zimmermann, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240

[2] Synthesis of 3-tetrazolylmethyl-4H-chromen-4-ones via Ugi-azide and biological evaluation against Entamoeba histolytica, Giardia lamblia and Trichomona vaginalis [J].

Cano, Pedro A. ;

Islas-Jacome, Alejandro ;

Gonzalez-Marrero, Joaquin ;

Yepez-Mulia, Lilian ;

Calzada, Fernando ;

Gomez-Montano, Rocio .

BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (04) :1370-1376

[3] Synthesis of 2-Tetrazolylmethyl-2,3,4,9-tetrahydro-1H-β-carbolines by a One-Pot Ugi-Azide/Pictet-Spengler Process [J].

Cardenas-Galindo, Luis E. ;

Islas-Jacome, Alejandro ;

Alvarez-Rodriguez, Nancy V. ;

El Kaim, Laurent ;

Gamez-Montano, Rocio .

SYNTHESIS-STUTTGART, 2014, 46 (01) :49-56

[4] Process Research and Development for a Tetrazole-Based Growth Hormone Secretagogue (GHS) Pharmaceutical Development Candidate [J].

Davulcu, Akin H. ;

McLeod, Douglas D. ;

Li, Jun ;

Katipally, Kishta ;

Littke, Adam ;

Doubleday, Wendel ;

Xu, Zhongmin ;

McConlogue, Cary W. ;

Lai, Chiajen. J. ;

Gleeson, Margaret ;

Schwinden, Mark ;

Parsons, Rodney L., Jr. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (11) :4068-4079

[5] Beyond the Ugi reaction: less conventional interactions between isocyanides and iminium species [J].

El Kaim, Laurent ;

Grimaud, Laurence .

TETRAHEDRON, 2009, 65 (11) :2153-2171

[6] Efficient sensitization of lanthanide luminescence by tetrazole-based polydentate ligands [J].

Giraud, Marion ;

Andreiadis, Eugen S. ;

Fisyuk, Alexander S. ;

Demadrille, Renaud ;

Pecaut, Jacques ;

Imbert, Daniel ;

Mazzanti, Marinella .

INORGANIC CHEMISTRY, 2008, 47 (10) :3952-3954

[7] Synthesis of 3-tetrazolylmethyl-azepino[4,5-b]indol-4-ones in two reaction steps: (Ugi-azide/N-acylation/SN2)/free radical cyclization and docking studies to a 5-Ht6 model [J].

Gordillo-Cruz, Raul E. ;

Renteria-Gomez, Angel ;

Islas-Jacome, Alejandro ;

Cortes-Garcia, Carlos J. ;

Diaz-Cervantes, Erik ;

Robles, Juvencio ;

Gamez-Montano, Rocio .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (38) :6470-6476

[8] Mechanisms of tetrazole formation by addition of azide to nitriles [J].

Himo, F ;

Demko, ZP ;

Noodleman, L ;

Sharpless, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (41) :12210-12216

[9] A review of syntheses of 1,5-disubstituted tetrazole derivatives [J].

Sarvary, Afshin ;

Maleki, Ali .

MOLECULAR DIVERSITY, 2015, 19 (01) :189-212

[10] Aminomethyltetrazoles as potential inhibitors of the γ-aminobutyric acid transporters mGAT1-mGAT4: Synthesis and biological evaluation [J].

Schaffert, Eva S. ;

Hoefner, Georg ;

Wanner, Klaus T. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (21) :6492-6504

← 1 2 →