Synthesis of 2,5-Disubstituted Oxazoles from Arylacetylenes and -Amino Acids through an I2/Cu(NO3)2•3H2O-Assisted Domino Sequence

被引：9

作者：

Wang, Jungang ^{[1
]}

Cheng, Yan ^{[2
]}

Xiang, Jiachen ^{[2
]}

Wu, Anxin ^{[2
]}

机构：

[1] Guizhou Minzu Univ, Sch Chem Engn, Guiyang 550025, Guizhou, Peoples R China

[2] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Hubei, Peoples R China

来源：

SYNLETT | 2019年 / 30卷 / 06期

基金：

中国国家自然科学基金;

关键词：

oxazoles; -amino acids; copper catalysis; cascade reactions; alkynes; ONE-POT SYNTHESIS; C-H FUNCTIONALIZATION; N-PROPARGYL AMIDES; 2,4,5-TRISUBSTITUTED OXAZOLES; REGIOSELECTIVE SYNTHESIS; BENZAMIDINES HYDROCHLORIDE; SUBSTITUTED OXAZOLES; SELECTIVE SYNTHESIS; TERMINAL ALKYNES; 2+2+1 ANNULATION;

D O I：

10.1055/s-0037-1612087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new strategy has been developed for the synthesis of 2,5disubstituted oxazoles from easily available arylacetylenes and a- amino acids in the presence of Cu( NO3) 23H2O and iodine. This reaction process involves the I2/ Cu( NO3) 2 3H2O- assisted transformation of arylacetylene to a- iodo acetophenone, Kornblum oxidation to phenylglyoxal, condensation to imine, decarboxylation/ annulation/ oxidation reaction sequence to approach 2,5- disubstituted oxazoles.

引用

页码：743 / 747

页数：5

共 78 条

[1] Catalytic Cycloisomerization-Fluorination Sequence of N-Propargyl Amides by Iodoarene/HFPyridine/Selectfluor Systems [J].

Asari, Naoki ;

Takemoto, Yusuke ;

Shinomoto, Yukino ;

Yagyu, Takuma ;

Yoshimura, Akira ;

Zhdankin, Viktor V. ;

Saito, Akio .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (11) :1314-1317

[2] A two-stage iterative process for the synthesis of poly-oxazoles [J].

Atkins, JM ;

Vedejs, E .

ORGANIC LETTERS, 2005, 7 (15) :3351-3354

[3] Synthesis of (±)-cis-Clavicipitic Acid by a Rh(I)-Catalyzed Intramolecular Imine Reaction [J].

Bartoccini, Francesca ;

Casoli, Mariangela ;

Mari, Michele ;

Piersanti, Giovanni .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (07) :3255-3259

[4] Microwave-Assisted Cerium(III)-Promoted Cyclization of Propargyl Amides to Polysubstituted Oxazole Derivatives [J].

Bartoli, Giuseppe ;

Cimarelli, Cristina ;

Cipolletti, Roberto ;

Diomedi, Simone ;

Giovannini, Riccardo ;

Mari, Margherita ;

Marsili, Laura ;

Marcantoni, Enrico .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (03) :630-636

[5] Safe and Fast Flow Synthesis of Functionalized Oxazoles with Molecular Oxygen in a Microstructured Reactor [J].

Bay, Sarah ;

Baumeister, Tobias ;

Hashmi, A. Stephen K. ;

Roeder, Thorsten .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2016, 20 (07) :1297-1304

[6] The Copper-Catalyzed Decarboxylative Coupling of the sp3-Hybridized Carbon Atoms of α-Amino Acids [J].

Bi, Hai-Peng ;

Zhao, Liang ;

Liang, Yong-Min ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (04) :792-795

[7] Regioselective Formation of 2,5-Disubstituted Oxazoles Via Copper(I)-Catalyzed Cycloaddition of Acyl Azides and 1-Alkynes [J].

Cano, Israel ;

Alvares, Eleuterio ;

Carmen Nicasio, M. ;

Perez, Pedro J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (02) :191-193

[8] Alkyl Propiolates Participated [3+2] Annulation for the Switchable Synthesis of 1,5-and 1,4-Disubstituted 1,2,3-Triazoles Containing Ester Side Chain [J].

Cao, Shuo ;

Liu, Yunyun ;

Hu, Changfeng ;

Wen, Chengping ;

Wan, Jie-Ping .

CHEMCATCHEM, 2018, 10 (21) :5021-5025

[9] Synthesis of Substituted Oxazoles by Visible-Light Photocatalysis [J].

Chatterjee, Tanmay ;

Cho, Ji Young ;

Cho, Eun Jin .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16) :6995-7000

[10] Iterative oxazole assembly via α-chloroglycinates:: Total synthesis of (-)-muscoride A [J].

Coqueron, PY ;

Didier, C ;

Ciufolini, MA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (12) :1411-1414

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