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

[1] 2,2,2-Trifluoroethyl Oxalates in the One-Pot Parallel Synthesis of Hindered Aliphatic Oxamides
Bogolubsky, Andrey V.
Moroz, Yurii S.
Mykhailiuk, Pavel K.
Pipko, Sergey E.
Grishchenko, Alexander V.
Zhemera, Anton V.
Konovets, Anzhelika I.
Doroschuk, Roman A.
Dmytriv, Yurii V.
Zaporozhets, Olga A.
Tolmachev, Andrey
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (12) : 2120 - 2130
[2] Bis(2,2,2-trifluoroethyl) Carbonate as a Condensing Agent in One-Pot Parallel Synthesis of Unsymmetrical Aliphatic Ureas
Bogolubsky, Andrey V.
Moroz, Yurii S.
Mykhailiuk, Pavel K.
Granat, Dmitry S.
Pipko, Sergey E.
Konovets, Anzhelika I.
Doroschuk, Roman
Tomachev, Andrey
ACS COMBINATORIAL SCIENCE, 2014, 16 (06) : 303 - 308
[3] Facile synthesis of N2-substituted-1,2,3-triazole from aryl ethynylene and azide via a one-pot two-step strategy
Guan, Cong
Ji, Jian
Li, Zi
Wei, Qinghua
Wu, Xiang
Liu, Shunying
TETRAHEDRON, 2022, 108
[4] One-pot synthesis of new 6-pyrrolyl-N-alkyl-indazoles from reductive coupling of N-alkyl-6-nitroindazoles and 2,5-hexadione
El Ghozlani, Mohamed
Chicha, Hakima
Abbassi, Najat
Chigr, Mohamed
El Ammari, Lahcen
Saadi, Mohamed
Spinelli, Domenico
Rakib, El Mostapha
TETRAHEDRON LETTERS, 2016, 57 (01) : 113 - 117
[5] An efficient one-pot synthesis of N-(substituted phenyl)-1,2,5-thiadiazolidine-2-carboxamide 1,1-dioxide derivatives
Hessainia, Sihem
Boukhari, Abbes
Cheraiet, Zinelaabidine
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (01) : 218 - 224
[6] ONE-POT SYNTHESIS OF 2-SUBSTITUTED 3-THIOXO-2,3-DIHYDRO-1H-ISOINDOL-1-ONES BY THE REACTION OF N-SUBSTITUTED 2,N-DILITHIOBENZAMIDES WITH ISOTHIOCYANATES
Kobayashi, Kazuhiro
Fujiwara, Daiki
HETEROCYCLES, 2017, 94 (09) : 1759 - 1765
[7] Simple and Efficient One-Pot Synthesis of 2-Substituted Benzimidazoles from -Diaminoarene and Aryl Aldehydes
Alapati, Mohan Lakshmi Punna Rao
Abburi, Sridhar Rao
Mukkamala, Saratchandra Babu
Rao, M. Krishnaji
SYNTHETIC COMMUNICATIONS, 2015, 45 (21) : 2436 - 2443
[8] A one-pot multi-component synthesis of N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates catalysed by oxalic acid dihydrate
Sajadikhah, Seyed Sajad
Hazeri, Nourallah
Maghsoodlou, Malek Taher
Habibi-Khorassani, Sayyed Mostafa
Khandan-Barani, Khatereh
JOURNAL OF CHEMICAL RESEARCH, 2013, (01) : 40 - 42
[9] One-Pot Synthesis of N-Dichloroacetyl-2-methyl-2-phenylethyl-1,3-oxazolidine
Wang, Yong
Ye, Fei
Guo, Minghui
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 29 (02) : 195 - 198
[10] A facile and efficient synthesis of 2,2,2-trifluoroethyl 2-[(E)-N-phenylcinnamamido]-2-phenylacetates in trifluoroethanol via sequential Ugi four-component reaction/esterification
Balalaie, Saeed
Motaghedi, Hassan
Tahmassebi, Daryoush
Bararjanian, Morteza
Bijanzadeh, Hamid Reza
TETRAHEDRON LETTERS, 2012, 53 (46) : 6177 - 6181

← 1 2 3 4 5 →