One-pot cyclization/decarboxylation of α-keto acids and acylhydrazines for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles under transition-metal-free conditions

被引：18

作者：

Gao, Peng ^{[1
]}

Wang, Juan ^{[1
]}

Bai, Zijing ^{[1
]}

Cheng, Hualei ^{[1
]}

Xiao, Jian ^{[1
]}

Lai, Mengnan ^{[1
]}

Yang, Desuo ^{[1
]}

Fan, Mingjin ^{[1
]}

机构：

[1] Baoji Univ Arts & Sci, Coll Chem & Chem Engn, Shaanxi Key Lab Phytochem, Baoji 721013, Shaanxi, Peoples R China

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 41期

关键词：

Cyclization; Decarboxylation; Oxidation; Transition-metal-free reactions; Iodide; CARBOXYLIC-ACIDS; BOND FORMATION; 2,5-SUBSTITUTED 1,3,4-OXADIAZOLES; MICROWAVE IRRADIATION; CONVENIENT SYNTHESIS; COUPLING REACTIONS; MOLECULAR-IODINE; LIQUID-CRYSTALS; CINNAMIC-ACIDS; AMINO-ACIDS;

D O I：

10.1016/j.tetlet.2016.09.007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot KI/TBHP-mediated oxidative cyclization of alpha-keto acids with acylhydrazines was developed. A series of functional 2,5-disubstituted 1,3,4-oxadiazoles were synthesized through a tandem keto amine condensation followed by oxidative cyclization and decarboxylation reactions. This procedure was achieved under transition-metal-free conditions and showed advantages including readily available materials, mild reaction conditions and good group tolerance. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：4616 / 4619

页数：4

共 60 条

[1] DECARBOXYLATIVE IODINATION - A CONVENIENT SYNTHESIS OF BRIDGEHEAD IODIDES
ABEYWICKREMA, RS
DELLA, EW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (21) : 4226 - 4229
[2] A CONVENIENT SYNTHESIS OF ALKYL AND ARYL SUBSTITUTED BIS-1,3,4-OXADIAZOLES
ALTALIB, M
TASHTOUSH, H
ODEH, N
[J]. SYNTHETIC COMMUNICATIONS, 1990, 20 (12) : 1811 - 1817
[3] 1,3,4-Oxadiazoles: An emerging scaffold to target growth factors, enzymes and kinases as anticancer agents
Bajaj, Shalini
Asati, Vivek
Singh, Jagadish
Roy, Partha Pratim
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 97 : 124 - 141
[4] New approaches for decarboxylative biaryl coupling
Baudoin, Olivier
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) : 1373 - 1375
[5] Environmentally benign metal-free decarboxylative aldol and Mannich reactions
Baudoux, Jerome
Lefebvre, Pierre
Legay, Remi
Lasne, Marie-Claire
Rouden, Jacques
[J]. GREEN CHEMISTRY, 2010, 12 (02) : 252 - 259
[6] Behenna DC, 2012, NAT CHEM, V4, P130, DOI [10.1038/nchem.1222, 10.1038/NCHEM.1222]
[7] Design, Synthesis and Optoelectronic Properties of Unsymmetrical Oxadiazole Based Indene Substituted Derivatives as Deep Blue Fluoroscent Materials
Belavagi, Ningaraddi S.
Deshapande, Narahari
Pujar, G. H.
Wari, M. N.
Inamdar, S. R.
Khazi, Imtiyaz Ahmed M.
[J]. JOURNAL OF FLUORESCENCE, 2015, 25 (05) : 1323 - 1330
[8] Decarboxylative Ketone Aldol Reactions: Development and Mechanistic Evaluation under Metal-Free Conditions
Blaquiere, Nicole
Shore, Daniel G.
Rousseaux, Sophie
Fagnou, Keith
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) : 6190 - 6198
[9] Oxadiazoles in Medicinal Chemistry
Bostrom, Jonas
Hogner, Anders
Llinas, Antonio
Wellner, Eric
Plowright, Alleyn T.
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (05) : 1817 - 1830
[10] 1,3,4-oxadiazole formation as traceless release in solid phase organic synthesis
Cesarini, Sara
Colombo, Nicoletta
Pulici, Maurizio
Felder, Eduard R.
Brill, Wolfgang K. -D.
[J]. TETRAHEDRON, 2006, 62 (43) : 10223 - 10236

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