I2/KI-Mediated Oxidative N-N Bond Formation for the Synthesis of 1,5-Fused 1,2,4-Triazoles from N-Aryl Amidines

被引：70

作者：

Song, Lina ^{[1
]}

Tian, Xianhai ^{[1
]}

Lv, Zhigang ^{[1
]}

Li, Ertong ^{[1
]}

Wu, Jie ^{[1
]}

Liu, Yangxue ^{[1
]}

Yu, Wenquan ^{[1
]}

Chang, Junbiao ^{[1
,2
]}

机构：

[1] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Henan, Peoples R China

[2] Collaborat Innovat Ctr New Drug Res & Safety Eval, Zhengzhou 450001, Henan Province, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 14期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

MOLECULAR-IODINE; ORGANIC-SYNTHESIS; METAL-FREE; SELECTIVE INHIBITOR; DERIVATIVES; DISCOVERY; EFFICIENT; TRIAZOLOPYRIDINES; ALDEHYDES; SYSTEM;

D O I：

10.1021/acs.joc.5b01183

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An I-2/KI-mediated oxidative N-N bond formation reaction is described. This new and environmentally benign approach allows for the convenient synthesis of a variety of 1,2,4-triazolo [1,5-a]pyridines and other 1,5-fused 1,2,4-triazoles from readily available N-aryl amidines in an efficient and scalable fashion.

引用

页码：7219 / 7225

页数：7

共 33 条

[1]

Banerjee AK, 2006, J SCI IND RES INDIA, V65, P299

[2] Cu-Catalyzed Aerobic Oxidative Cyclization of Guanidylpyridines and Derivatives [J].

Bartels, Bjoern ;

Bolas, Conor Gordon ;

Cueni, Philipp ;

Fantasia, Serena ;

Gaeng, Nicolas ;

Trita, Andrada Stefania .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (02) :1249-1257

[3] SAR studies around a series of triazolopyridines as potent and selective PI3Kγ inhibitors [J].

Bell, Kathryn ;

Sunose, Mihiro ;

Ellard, Katie ;

Cansfield, Andrew ;

Taylor, Jess ;

Miller, Warren ;

Ramsden, Nigel ;

Bergamini, Giovanna ;

Neubauer, Gitte .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (16) :5257-5263

[4]

Bergamini G, 2012, NAT CHEM BIOL, V8, P576, DOI [10.1038/NCHEMBIO.957, 10.1038/nchembio.957]

[5] A Selective, Orally Bioavailable 1,2,4-Triazolo[1;5-a]pyridine-Based Inhibitor of Janus Kinase 2 for Use in Anticancer Therapy: Discovery of CEP-33779 [J].

Dugan, Benjamin J. ;

Gingrich, Diane E. ;

Mesaros, Eugen F. ;

Milkiewicz, Karen L. ;

Curry, Matthew A. ;

Zulli, Allison L. ;

Dobrzanski, Pawel ;

Serdikoff, Cynthia ;

Jan, Mahfuza ;

Angeles, Thelma S. ;

Albom, Mark S. ;

Mason, Jennifer L. ;

Aimone, Lisa D. ;

Meyer, Sheryl L. ;

Huang, Zeqi ;

Wells-Knecht, Kevin J. ;

Ator, Mark A. ;

Ruggeri, Bruce A. ;

Dorsey, Bruce D. .

JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (11) :5243-5254

[6] Iodine in Modern Oxidation Catalysis [J].

Finkbeiner, Peter ;

Nachtsheim, Boris J. .

SYNTHESIS-STUTTGART, 2013, 45 (08) :979-999

[7] SYNTHESIS OF 1H-1,2,4-TRIAZOLE 2-OXIDES AND ANNELATED DERIVATIVES [J].

GILCHRIST, TL ;

HARRIS, CJ ;

HAWKINS, DG ;

MOODY, CJ ;

REES, CW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (20) :2166-2170

[8] Transition-metal- and organic-solvent-free: a highly efficient anaerobic process for selective oxidation of alcohols to aldehydes and ketones in water [J].

Gogoi, P ;

Konwar, D .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (19) :3473-3475

[9] NOVEL PREPARATION OF BENZIMIDAZOLES FROM N-ARYLAMIDINES . NEW SYNTHESIS OF THIABENDAZOLE [J].

GRENDA, VJ ;

JONES, RE ;

GAL, G ;

SLETZING.M .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (01) :259-&

[10] Iodine-catalyzed transformation of molecules containing oxygen functional groups [J].

Jereb, Marjan ;

Vrazic, Dejan ;

Zupan, Marko .

TETRAHEDRON, 2011, 67 (07) :1355-1387

← 1 2 3 4 →