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

[11] Biotransformation reactions of five-membered aromatic heterocyclic rings [J].

Dalvie, DK ;

Kalgutkar, AS ;

Khojasteh-Bakht, SC ;

Obach, RS ;

O'Donnell, JP .

CHEMICAL RESEARCH IN TOXICOLOGY, 2002, 15 (03) :269-299

[12] Intermolecular and Selective Synthesis of 2,4,5-Trisubstituted Oxazoles by a Gold-Catalyzed Formal [3+2] Cycloaddition [J].

Davies, Paul W. ;

Cremonesi, Alex ;

Dumitrescu, Lidia .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (38) :8931-8935

[13] Thiazole and Oxazole Alkaloids: Isolation and Synthesis [J].

Davyt, Danilo ;

Serra, Gloria .

MARINE DRUGS, 2010, 8 (11) :2755-2780

[14] Total synthesis of tubulysin U and V [J].

Doemling, Alexander ;

Beck, Barbara ;

Eichelberger, Uwe ;

Sakamuri, Sukumar ;

Menon, Sanjay ;

Chen, Quin-Zene ;

Lu, Yingchun ;

Wessjohann, Ludger A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (43) :7235-7239

[15] Cu(II)-aza(bisoxazoline)-catalyzed asymmetric benzoylations [J].

Gissibl, A ;

Finn, MG ;

Reiser, O .

ORGANIC LETTERS, 2005, 7 (12) :2325-2328

[16] Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles [J].

Gulevich, Anton V. ;

Dudnik, Alexander S. ;

Chernyak, Natalia ;

Gevorgyan, Vladimir .

CHEMICAL REVIEWS, 2013, 113 (05) :3084-3213

[17] Regioselective Synthesis of 5-Aminooxazoles via Cp*Co(III)-Catalyzed Formal [3+2] Cycloaddition of N-(Pivaloyloxy)amides with Ynamides [J].

Han, Xiang-Lei ;

Zhou, Chu-Jun ;

Liu, Xu-Ge ;

Zhang, Shang-Shi ;

Wang, Honggen ;

Li, Qingjiang .

ORGANIC LETTERS, 2017, 19 (22) :6108-6111

[18] 4-(4-cycloalkyl/aryl-oxazol-5-yl)benzenesulfonamides as selective cyclooxygenase-2 inhibitors:: Enhancement of the selectivity by introduction of a fluorine atom and identification of a potent, highly selective, and orally active COX-2 inhibitor JTE-5221 [J].

Hashimoto, H ;

Imamura, K ;

Haruta, J ;

Wakitani, K .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (07) :1511-1517

[19] From Propargylic Amides to Functionalized Oxazoles: Domino Gold Catalysis/Oxidation by Dioxygen [J].

Hashmi, A. Stephen K. ;

Jaimes, Maria Camila Blanco ;

Schuster, Andreas M. ;

Rominger, Frank .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (15) :6394-6408

[20] An Efficient [2+2+1] Synthesis of 2,5-Disubstituted Oxazoles via Gold-Catalyzed Intermolecular Alkyne Oxidation [J].

He, Weimin ;

Li, Chaoqun ;

Zhang, Liming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (22) :8482-8485

← 1 2 3 4 5 6 7 8 →