One-pot synthesis of oxoisoindoline-1,2,3-triazole hybrid by a Ugi-click reaction

被引：10

作者：

Akrami, Sara ^{[1
]}

Firoozpour, Loghman ^{[2
]}

Goli-Garmroodi, Fereshteh ^{[3
,4
]}

Moghimi, Setareh ^{[3
,4
]}

Mahdavi, Mohammad ^{[2
]}

Zonouzi, Afsaneh ^{[1
]}

Foroumadi, Alireza ^{[2
,3
,4
,5
,6
]}

机构：

[1] Univ Tehran, Sch Chem, Coll Sci, Tehran, Iran

[2] Univ Tehran Med Sci, Drug Design & Dev Res Ctr, Tehran, Iran

[3] Univ Tehran Med Sci, Fac Pharm, Dept Med Chem, Tehran, Iran

[4] Univ Tehran Med Sci, Pharmaceut Sci Res Ctr, Tehran, Iran

[5] Kerman Univ Med Sci, Inst Neuropharmacol, Fac Pharm, Dept Med Chem, Kerman, Iran

[6] Kerman Univ Med Sci, Inst Neuropharmacol, Neurosci Res Ctr, Kerman, Iran

来源：

SYNTHETIC COMMUNICATIONS | 2016年 / 46卷 / 20期

基金：

美国国家科学基金会;

关键词：

Click reaction; multicomponent reaction; one-pot synthesis; 1,2,3-triazole; Ugi reaction; MULTICOMPONENT REACTIONS; INHIBITORS; DERIVATIVES; TRANSFORMATIONS; DISCOVERY;

D O I：

10.1080/00397911.2016.1223313

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,2,3-Triazole-3-oxoisoindoline-1-carboxamide system was successfully synthesized by using a combination of Ugi and click reactions. This two-step, one-pot synthesis was started by the reaction of 2-formyl benzoic acid, propargyl amine, and cyclohexyl isocyanide in ethanol. The resultant Ugi adduct underwent a copper-catalyzed click reaction, producing the desired products in good yields. [GRAPHICS] .

引用

页码：1708 / 1712

页数：5

共 36 条

[1] [Anonymous], 1984, 1 3 DIPOLAR CYCLOADD
[2] Reaction of Isatoic Anhydride, Amine, and N,N′-Dialkyl Carbodiimides Under Solvent-Free Conditions: New and Efficient Synthesis of 3-Alkyl-2-(alkylamino)quinazolin-4(3H)-ones
Asadi, Mehdi
Ebrahimi, Mostafa
Mahdavi, Mohammad
Saeedi, Mina
Ranjbar, Parviz Rashidi
Yazdani, Farshad
Shafiee, Abbas
Foroumadi, Alireza
[J]. SYNTHETIC COMMUNICATIONS, 2013, 43 (17) : 2385 - 2392
[3] Banfi L, 2010, TOP HETEROCYCL CHEM, V23, P1, DOI 10.1007/7081_2009_23
[4] CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective
Bock, VD
Hiemstra, H
van Maarseveen, JH
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) : 51 - 68
[5] Design, Synthesis, and Preliminary Biological Evaluation of Pyrrolo[3,4-c]quinolin-1-one and Oxoisoindoline Derivatives as Aggrecanase Inhibitors
Cappelli, Andrea
Nannicini, Chiara
Valenti, Salvatore
Giuliani, Germano
Anzini, Maurizio
Mennuni, Laura
Giordani, Antonio
Caselli, Gianfranco
Stasi, Luigi Piero
Makovec, Francesco
Giorgi, Gianluca
Vomero, Salvatore
[J]. CHEMMEDCHEM, 2010, 5 (05) : 739 - 748
[6] Virtual Screening and Computational Optimization for the Discovery of Covalent Prolyl Oligopeptidase Inhibitors with Activity in Human Cells
De Cesco, Stephane
Deslandes, Sebastien
Therrien, Eric
Levan, David
Cueto, Mickael
Schmidt, Ralf
Cantin, Louis-David
Mittermaier, Anthony
Juilerat-Jeanneret, Lucienne
Moitessier, Nicolas
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (14) : 6306 - 6315
[7] Dehne H., 1994, In Methoden der Organischen Chemie (Houben-Weyl), Schaumann, V8, P305
[8] Recent developments in isocyanide based multicomponent reactions in applied chemistry
Dömling, A
[J]. CHEMICAL REVIEWS, 2006, 106 (01) : 17 - 89
[9] GREEN AND CATALYST-FREE ONE-POT SYNTHESIS OF ANTHRANILAMIDE SCHIFF BASES: AN APPROACH TOWARD SIRTINOL
Ebrahimi, Seyed Mostafa
Mahdavi, Mohammad
Emami, Saeed
Saeedi, Mina
Asadi, Mehdi
Firoozpour, Loghman
Khoobi, Mehdi
Divsalar, Kouros
Shafiee, Abbas
Foroumadi, Alireza
[J]. SYNTHETIC COMMUNICATIONS, 2014, 44 (05) : 665 - 673
[10] Synthesis and evaluation of novel quinazolinone-1,2,3-triazoles as inhibitors of lipoxygenase
Farjadmand, Fatemeh
Arshadi, Hossein
Moghimi, Setareh
Nadri, Hamid
Moradi, Alireza
Eghtedari, Mohammad
Jafarpour, Farnaz
Mahdavi, Mohammad
Shafiee, Abbas
Foroumadi, Alireza
[J]. JOURNAL OF CHEMICAL RESEARCH, 2016, (03) : 188 - 191

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