Three-component reaction of ketals, isonitriles, and trimethylsilyl azide

被引:6
作者
Golantsov, Nikita E. [1 ]
Nguyen, Hung M. [1 ]
Varlamov, Aleksey V. [1 ]
Aksenov, Aleksander V. [2 ]
Voskressensky, Leonid G. [1 ]
机构
[1] Peoples Friendship Univ Russia, 6 Miklukho Maklaya St, Moscow 117198, Russia
[2] North Caucasus Fed Univ, 1 Pushkina St, Stavropol 355009, Russia
基金
俄罗斯基础研究基金会;
关键词
isonitrile; ketal; tetrazole; trimethylsilyl azide; Passerini reaction; ISOCYANIDES; TETRAZOLES; INSERTION;
D O I
10.1007/s10593-017-2073-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] . It was demonstrated that a ZnCl2-catalyzed three-component reaction of ketals, isonitriles, and trimethylsilyl azide led to 1,5-disubstituted tetrazoles in moderate to high yields.
引用
收藏
页码:446 / 450
页数:5
相关论文
共 21 条
[1]   Structure-activity relationship of novel series of 1,5-disubstituted tetrazoles as cyclooxygenase-2 inhibitors: Design, synthesis, bioassay screening and molecular docking studies [J].
Al-Hourani, Baker Jawabrah ;
Al-Awaida, Wajdy ;
Matalka, Khalid Z. ;
El-Barghouthi, Musa I. ;
Alsoubani, Fatima ;
Wuest, Frank .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (19) :4757-4762
[2]  
Banfi L., 2005, Organic Reactions, V65, P1, DOI [10.1002/0471264180.or065.01, DOI 10.1002/0471264180.0R065.01]
[3]   Synthesis of tetrazolodiazepines by a five-centered four-component azide Ugi reaction. Scope and limitations [J].
Borisov, R. S. ;
Polyakov, A. I. ;
Medvedeva, L. A. ;
Guranova, N. I. ;
Voskressensky, L. G. .
RUSSIAN CHEMICAL BULLETIN, 2012, 61 (08) :1609-1615
[4]   A Concise Approach Toward Tetrazolyl-Substituted Benzazocines via a Novel Isocyanide-Based Multicomponent Reaction [J].
Borisov, Roman S. ;
Voskressensky, Leonid G. ;
Polyakov, Anatoly I. ;
Borisova, Tatiana N. ;
Varlamov, Alexey V. .
SYNLETT, 2014, 25 (07) :955-958
[5]   Concise Approach toward Tetrazolo[1,5-a][1,4]benzodiazepines via a Novel Multicomponent Isocyanide-Based Condensation [J].
Borisov, Roman S. ;
Polyakov, Anatoliy I. ;
Medvedeva, Lidia A. ;
Khrustalev, Victor N. ;
Guranova, Natalia I. ;
Voskressensky, Leonid G. .
ORGANIC LETTERS, 2010, 12 (17) :3894-3897
[6]   An efficient Passerini tetrazole reaction (PT-3CR) [J].
Chandgude, Ajay L. ;
Domling, Alexander .
GREEN CHEMISTRY, 2016, 18 (13) :3718-3721
[7]   Convergent Three-Component Tetrazole Synthesis [J].
Chandgude, Ajay L. ;
Domling, Alexander .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (14) :2383-2387
[8]   A versatile ethanolamine-derived trifluoromethyl enaminone ligand for the elaboration of nickel(II) and copper(II)-dysprosium(III) multinuclear complexes with magnetic properties [J].
Chopin, Nicolas ;
Novitchi, Ghenadie ;
Medebielle, Maurice ;
Pilet, Guillaume .
JOURNAL OF FLUORINE CHEMISTRY, 2015, 179 :169-174
[9]   Methyl homologues of methyljasmonate and methyl dihydrojasmonate (Hedione®) from sorbyl alcohol [J].
Giersch, W ;
Farris, I .
HELVETICA CHIMICA ACTA, 2004, 87 (07) :1601-1606
[10]   Phenyltetrazolyl-phenylamides: Substituent impact on modulation capability and selectivity toward the efflux protein ABCG2 and investigation of interaction with the transporter [J].
Koehler, Sebastian C. ;
Silbermann, Katja ;
Wiese, Michael .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 124 :881-895