A novel route to 2,3-pyrazol-1(5H)-ones via palladium-catalyzed carbonylation of 1,2-diaza-1,3-butadienes

被引：64
作者：
Boeckman, RK [1 ]
Reed, JE [1 ]
Ge, P [1 ]
机构：
[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
来源：
ORGANIC LETTERS | 2001年 / 3卷 / 23期
关键词：
D O I：
10.1021/ol016565x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] A novel Pd(0)-catalyzed carbonylation of both isolable 1,2-diaza-1,3-butadienes and those generated in situ by extrusion of SO2 and CO2 from heterocyclic precursors is described. The reaction proceeds at room temperature to 110 degreesC under 1-2 atm of CO to afford 2,3-pyrazol-1(5H)-ones in good to excellent yields. The effect of catalyst structure and stability on the carbonylation reaction is evaluated.
引用
收藏
页码：3651 / 3653
页数：3
相关论文
共 50 条
[21]   Palladium-catalyzed Csp2-H carbonylation of aromatic oximes: selective access to benzo[d][1,2] oxazin-1-ones and 3-methyleneisoindolin-1-ones [J].
Xu, Yanli ;
Hu, Weigao ;
Tang, Xiaodong ;
Zhao, Jinwu ;
Wu, Wanqing ;
Jiang, Huanfeng .
CHEMICAL COMMUNICATIONS, 2015, 51 (31) :6843-6846
[22]   First preparation and reaction of polymer-bound 1,2-diaza-1,3-butadienes. A convenient entry to 4-triphenylphosphoranylidene-4,5-dihydropyrazol-5-ones [J].
Attanasi, OA ;
Filippone, P ;
Guidi, B ;
Hippe, T ;
Mantellini, F ;
Tietze, LF .
TETRAHEDRON LETTERS, 1999, 40 (52) :9277-9280
[23]   1,3-Dipolar cycloaddition of azomethine imines to ethynyl hetarenes: A synthetic route to 2,3-dihydropyrazolo[1,2-a]pyrazol-1(5H)-one based heterobiaryls [J].
Nelina-Nemtseva, Julia I. ;
Gulevskaya, Anna V. ;
Suslonov, Vitaliy V. ;
Misharev, Alexander D. .
TETRAHEDRON, 2018, 74 (10) :1101-1109
[24]   Palladium-Catalyzed Oxidative Carbonylation of the Alkenyl C-H Bonds of Enamides: Synthesis of 1,3-Oxazin-6-ones [J].
Chen, Ming ;
Ren, Zhi-Hui ;
Wang, Yao-Yu ;
Guan, Zheng-Hui .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (52) :14196-14199
[25]   Regioselective synthesis of spiro-cyclopropanated 1-aminopyrrol-2-ones by Bi(OTf)3-catalyzed one-pot 'Mukaiyama-Michael addition/cyclization/ring-contraction' reactions of 1,2-bis(trimethylsilyloxy)cyclobutene with 1,2-diaza-1,3-butadienes [J].
Attanas, Orazio A. ;
Favi, Gianfranco ;
Giorgi, Gianluca ;
Mantellini, Fabio ;
Karapetyan, Vahuni ;
Langer, Peter .
TETRAHEDRON, 2009, 65 (28) :5456-5461
[26]   Copper-Catalyzed Synthesis of 5-Aryl-6-(Trifluoromethyl)-2,3-Dihydropyrazolo[1,2-a]Pyrazol-1(5H)-One [J].
Zhang, Xinyu ;
Wang, Hui ;
Xie, Lili ;
You, Chenhui ;
Han, Xiaoyan ;
Weng, Zhiqiang .
CHEMISTRY-AN ASIAN JOURNAL, 2021, 16 (18) :2669-2673
[27]   Double 1,4-addition of malonate to 1,2-diaza-1,3-butadienes: a useful route to previously unknown symmetric and unsymmetric 1,6-dioxo-2,7-diazaspiro[4.4]nona-3,8-dienes [J].
Attanasi, OA ;
De Crescentini, L ;
Filippone, P ;
Mantellini, F .
NEW JOURNAL OF CHEMISTRY, 2001, 25 (04) :534-537
[28]   Synthesis of 3-substituted-3,4-dihydro-2H-1,3-benzothiazin-2-ones via a highly regioselective palladium-catalyzed carbonylation of 2-substituted-2,3-dihydro-1,2-benzisothiazoles [J].
Rescourio, Gwenaella ;
Alper, Howard .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (04) :1612-1615
[29]   Diversity-oriented synthesis of functionalized 1-aminopyrroles by regioselective zinc chloride-catalyzed, one-pot 'Conjugate Addition/Cyclization' reactions of 1,3-bis(silyl enol ethers) with 1,2-diaza-1,3-butadienes [J].
Karapetyan, Vahuni ;
Mkrtchyan, Satenik ;
Schmidt, Andreas ;
Attanasi, Orazio A. ;
Favi, Gianfranco ;
Mantellini, Fabio ;
Villinger, Alexander ;
Fischer, Christine ;
Langer, Peter .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (09) :1331-1336
[30]   Enantioselective synthesis of 3,6-Dihydro-1H-pyridin-2-ones:: Unexpected regioselectivity in the palladium-catalyzed decarboxylative carbonylation of 5-vinyloxazolidin-2-ones [J].
Knight, JG ;
Ainge, SW ;
Harm, AM ;
Harwood, SJ ;
Maughan, HI ;
Armour, DR ;
Hollinshead, DM ;
Jaxa-Chamiec, AA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (12) :2944-2945
12345