2,2,2-Trifluoroethyl Chlorooxoacetate-Universal Reagent for One-Pot Parallel Synthesis of N1-Aryl-N2-alkyl-Substituted Oxamides

被引：7

作者：

Bogolubsky, Andrey V. ^{[1
]}

Moroz, Yurii S. ^{[1
,2
]}

Mykhailiuk, Pavel K. ^{[1
,3
]}

Pipko, Sergey E. ^{[2
]}

Zhemera, Anton V. ^{[1
]}

Konovets, Anzhelika I. ^{[1
,4
]}

Stepaniuk, Olena O. ^{[1
,5
]}

Myronchuk, Inna S. ^{[1
,5
]}

Dmytriv, Yurii V. ^{[1
]}

Doroschuk, Roman A. ^{[3
]}

Zaporozhets, Olga A. ^{[3
]}

Tolmachev, Andrey ^{[1
,2
]}

机构：

[1] Enamine Ltd, 78 Chervonotkatska St, UA-02094 Kiev, Ukraine

[2] Kyiv Natl Taras Shevchenko Univ, ChemBioCtr, UA-02094 Kiev, Ukraine

[3] Kyiv Natl Taras Shevchenko Univ, Dept Chem, UA-01601 Kiev, Ukraine

[4] Kyiv Natl Taras Shevchenko Univ, Inst High Technol, UA-03187 Kiev, Ukraine

[5] Natl Tech Univ Ukraine, Kyiv Politech Inst, UA-03056 Kiev, Ukraine

来源：

ACS COMBINATORIAL SCIENCE | 2015年 / 17卷 / 10期

关键词：

N-1-aryl-N-2-alkyl-substituted oxamides; parallel synthesis; one-pot approach; ethyl chlorooxoacetate; 2,2,2-trifluoroethyl chlorooxoacetate; N-HETEROCYCLIC CARBENES; ASYMMETRIC ALLYLIC SUBSTITUTION; ACID IONIZATION CONSTANTS; REDUCTIVE AMINATION; NHC LIGANDS; DESIGN; INHIBITORS; PHOSPHATES; MECHANISM; ALCOHOLS;

D O I：

10.1021/acscombsci.5b00091

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A one-pot parallel synthesis of N-1-aryl-N-2-alkyl-substituted oxamides with 2,2,2-trifluoroethyl chlorooxoacetate was developed. The synthesis of a library of 45 oxamides revealed higher efficiency of this reagent over the known ethyl chlorooxoacetate. The reagent was successfully used to prepare the known oxamide-containing HIV entry inhibitors.

引用

页码：615 / 622

页数：8

共 50 条

[41] An Effective Metal Free One-pot Synthesis of 5-Substituted-1,3,4-oxadiazole-2thiols and Symmetrical Diacylhydrazines Using Mukaiyama's Reagent [J].

Pandey, Rajesh K. ;

Kumar, Ashish ;

Pathak, Arunendra ;

Gupta, Monika ;

Rajput, Chatrasal S. .

INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2022, 32 (04) :531-538

[42] Microwave promoted one-pot synthesis of 2-aryl substituted 1,3,4-oxadiazoles and 1,2,4-oxadiazole derivatives using Al3+-K10 clay as a heterogeneous catalyst [J].

Suresh, Dhanusu ;

Kanagaraj, Kuppusamy ;

Pitchumani, Kasi .

TETRAHEDRON LETTERS, 2014, 55 (27) :3678-3682

[43] A simple and efficient approach to one-pot synthesis of mono- and bis-N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates catalyzed by InCl3 [J].

Sajadikhah, Seyed Sajad ;

Maghsoodlou, Malek Taher ;

Hazeri, Nourallah .

CHINESE CHEMICAL LETTERS, 2014, 25 (01) :58-60

[44] Regioselective N/C-Heterocyclization of Allenylindium Bromide Across Aryl Azides: One-Pot Synthesis of 5-Methyl-1,2,3-triazoles [J].

Banday, Abid H. ;

Hruby, Victor J. .

SYNLETT, 2014, 25 (13) :1859-1862

[45] A three component one-pot synthesis of N-amino-2-pyridone derivatives catalyzed by KF-Al2O3 [J].

Kshiar, B. ;

Shangpliang, O. R. ;

Myrboh, B. .

SYNTHETIC COMMUNICATIONS, 2018, 48 (14) :1816-1827

[46] One-Pot Three-Component Reaction for Synthesis of Highly Substituted Pyrazolo[1,2-a][1,2,4]triazole Derivatives [J].

Sajadikhah, Seyed S. ;

Maghsoodlou, Malek T. ;

Hazeri, Nourallah ;

Habibi-Khorassani, Sayyed M. .

LETTERS IN ORGANIC CHEMISTRY, 2011, 8 (10) :743-748

[47] Reaction between Benzoic Acid N′-(2-Oxo-2-Phenyl-Ethyl)Hydrazide and Acetylenic Esters in the Presence of Alkyl Isocyanides: One-Pot Synthesis of Highly Functionalized 2,3-Dihydro-1H-Pyrazoles [J].

Ardakani, Leili Shaker ;

Mosslemin, Mohammad H. ;

Hassanabadi, Alireza ;

Hashemian, Saeedeh .

POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (10) :6861-6867

[48] N-Iodosuccinimide involved one-pot metal-free synthesis of 2-heteroaromatic benzothiazole compounds [J].

Chu, Xianglong ;

Duan, Tiantian ;

Liu, Xuan ;

Feng, Lei ;

Jia, Jiong ;

Ma, Chen .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (07) :1606-1611

[49] Synthesis of Isoindolo[2,1-a]quinazoline-5,11-dione Derivatives via the Reductive One-Pot Reaction of N-Substituted 2-Nitrobenzamides and 2-Formylbenzoic Acids [J].

Mahdavi, Mohammad ;

Najafi, Ramin ;

Saeedi, Mina ;

Alipour, Eskandar ;

Shafiee, Abbas ;

Foroumadi, Alireza .

HELVETICA CHIMICA ACTA, 2013, 96 (03) :419-423

[50] An efficient three-component, one-pot synthesis of 2-alkylthio-4-amino-5-cyano-6-aryl(alkyl)pyrimidines in water [J].

Li, Qiao-Yan ;

Ge, Ze-Mei ;

Cheng, Tie-Ming ;

Li, Run-Tao .

MOLECULAR DIVERSITY, 2012, 16 (03) :431-439

← 1 2 3 4 5 →