Pd-Catalyzed Oxidative Annulation of Hydrazides with Isocyanides: Synthesis of 2-Amino-1,3,4-oxadiazoles

被引:96
作者
Fang, Tao [1 ]
Tan, Qitao [1 ]
Ding, Zhengwei [1 ]
Liu, Bingxin [1 ]
Xu, Bin [1 ,2 ,3 ]
机构
[1] Shanghai Univ, Dept Chem, Innovat Drug Res Ctr, Shanghai 200444, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[3] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
基金
中国国家自然科学基金;
关键词
BENZOIC-ACID HYDRAZIDES; N BOND FORMATION; X-RAY-STRUCTURE; VINBLASTINE ANALOGS; EFFICIENT ACCESS; MULTICOMPONENT REACTIONS; REGIOSELECTIVE SYNTHESIS; 3-COMPONENT REACTION; DIRECT AMINATION; INSERTION;
D O I
10.1021/ol5006449
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient palladium-catalyzed oxidative annulation reaction was developed through sequential isocyanide insertions into N-H and O-H bonds of hydrazides, which provides an efficient access to valuable 2-amino-1,3,4-oxadiazoles and their derivatives.
引用
收藏
页码:2342 / 2345
页数:4
相关论文
共 73 条
[1]   NICOTINOYL HYDRAZIDE COMPLEXES OF SOME 1ST ROW TRANSITION-METAL IONS [J].
AGGARWAL, RC ;
RAO, TR .
TRANSITION METAL CHEMISTRY, 1977, 2 (05) :201-204
[2]   From docking false-positive to active Anti-HIV agent [J].
Barreiro, Gabriela ;
Kim, Joseph T. ;
Guimares, Cristiano R. W. ;
Bailey, Christopher M. ;
Domaoal, Robert A. ;
Wang, Ligong ;
Anderson, Karen S. ;
Jorgensen, William L. .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (22) :5324-5329
[3]   A Powerful Palladium-Catalyzed Multicomponent Process for the Preparation of Oxazolines and Benzoxazoles [J].
Boissarie, Patrick J. ;
Hamilton, Zoe E. ;
Lang, Stuart ;
Murphy, John A. ;
Suckling, Colin J. .
ORGANIC LETTERS, 2011, 13 (23) :6256-6259
[4]   1,3,4-OXADIAZOLE, 1,3,4-THIADIAZOLE, AND 1,2,4-TRIAZOLE ANALOGS OF THE FENAMATES - IN-VITRO INHIBITION OF CYCLOOXYGENASE AND 5-LIPOXYGENASE ACTIVITIES [J].
BOSCHELLI, DH ;
CONNOR, DT ;
BORNEMEIER, DA ;
DYER, RD ;
KENNEDY, JA ;
KUIPERS, PJ ;
OKONKWO, GC ;
SCHRIER, DJ ;
WRIGHT, CD .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (13) :1802-1810
[5]   Oxadiazoles in Medicinal Chemistry [J].
Bostrom, Jonas ;
Hogner, Anders ;
Llinas, Antonio ;
Wellner, Eric ;
Plowright, Alleyn T. .
JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (05) :1817-1830
[6]   Novel procedure for the synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using polymer-supported Burgess reagent under microwave conditions [J].
Brain, CT ;
Paul, JM ;
Loong, Y ;
Oakley, PJ .
TETRAHEDRON LETTERS, 1999, 40 (16) :3275-3278
[7]   Transannular Diels-Alder/1,3-Dipolar Cycloaddition Cascade of 1,3,4-Oxadiazoles: Total Synthesis of a Unique Set of Vinblastine Analogues [J].
Campbell, Erica L. ;
Skepper, Colin K. ;
Sankar, Kuppusamy ;
Duncan, Katharine K. ;
Boger, Dale L. .
ORGANIC LETTERS, 2013, 15 (20) :5306-5309
[8]   SUBSTITUTED 1,3,4-THIADIAZOLES WITH ANTICONVULSANT ACTIVITY .4. AMIDINES [J].
CHAPLEO, CB ;
MYERS, PL ;
SMITH, ACB ;
STILLINGS, MR ;
TULLOCH, IF ;
WALTER, DS .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (01) :7-11
[9]   o-lodoxybenzoic Acid Mediated Oxidative Desulfurization Initiated Domino Reactions for Synthesis of Azoles [J].
Chaudhari, Pramod S. ;
Pathare, Sagar P. ;
Akamanchi, Krishnacharaya G. .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (08) :3716-3723
[10]   ACID-CATALYZED HYDROLYSES OF ACYLPYRROLES AND ACYLINDOLES - NONINVOLVEMENT OF PROTONATED SUBSTRATES [J].
CIPICIANI, A ;
LINDA, P ;
SAVELLI, G ;
BUNTON, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (16) :4874-4879