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

[31] Palladium-Catalyzed Synthesis of 1,2,3,4-Tetrahydro-5H-2-benzazepin-5-ones [J].

Okuro, Kazumi ;

Alper, Howard .

SYNLETT, 2012, (17) :2531-2533

[32] Regioselective synthesis of new 1-aminopyrroles and 1-amino-4,5,6,7-tetrahydroindoles by one-pot 'conjugate addition/cyclization' reactions of 1,3-bis(silyl enol ethers) with 1,2-diaza-1,3-butadienes [J].

Schmidt, Andreas ;

Karapetyana, Vahuni ;

Attanasi, Orazio A. ;

Favi, Gianfranco ;

Goerls, Helmar ;

Mantellini, Fabio ;

Langer, Peter .

SYNLETT, 2007, (19) :2965-2968

[33] Palladium-catalyzed oxidative carbonylation of hydrazides: synthesis of 1,3,4-oxadiazol-2(3H)-ones [J].

Wang, Yu ;

Meng, Xu ;

Yang, Yuting ;

Zhang, Lutao ;

Guo, Shuaibo ;

Tang, Dong ;

Li, Yaxuan ;

Chen, Baohua .

CHEMICAL COMMUNICATIONS, 2015, 51 (10) :1905-1907

[34] REACTION OF 1,4-DIAZA-1,3-BUTADIENES WITH CYANOTRIMETHYLSILANE - SYNTHESIS OF 2,3-BIS(ARYLAMINO)PROPENENITRILES AND THEIR CYCLIZATION TO 1,4-DIARYL-2,3-DIOXO-5-PYRAZINECARBONITRILES [J].

TAKAHASHI, M ;

MIYAHARA, H ;

YOSHIDA, N .

HETEROCYCLES, 1988, 27 (01) :155-160

[35] Palladium-catalyzed amino group arylation of 1,3-disubstituted 1H-pyrazol-5-amine based on Buchwald–Hartwig reaction [J].

Mateusz Kucharek ;

Andrzej Danel .

Chemistry of Heterocyclic Compounds, 2021, 57 :633-639

[36] Facile Assembly of Benzo[b]naphtho[2,3-d]azocin-6(5H)-ones by a Palladium-Catalyzed Double Carbometalation [J].

Gong, Xinxing ;

Chen, Mo ;

Yao, Liangqing ;

Wu, Jie .

CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (10) :1613-1617

[37] Palladium-Catalyzed Carbonylation-Decarboxylation of Diethyl(2-iodoaryl)malonates with Imidoyl Chlorides: An Efficient Route to Substituted Isoquinolin-1(2H)-ones [J].

Zheng, Zhaoyan ;

Alper, Howard .

ORGANIC LETTERS, 2008, 10 (21) :4903-4906

[38] A NOVEL SYNTHESIS OF 2,3-DIHYDRO[1,5]BENZOTHIAZEPIN-4(5H)-ONES [J].

LANCELOT, JC ;

LETOIS, B ;

SATURNINO, C ;

DECAPRARIIS, P ;

ROBBA, M .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1992, 24 (02) :204-208

[39] Palladium-catalyzed desulfonylative carbonylation reaction of benylsulfonyl chlorides with anthranils for the synthesis of 3-arylquinoin-2(1H)-ones [J].

Dai, Weiqi ;

Zhao, Ruyi ;

Qi, Xinxin ;

Wu, Xiao-Feng .

JOURNAL OF CATALYSIS, 2024, 429

[40] A General and Expedient Synthesis of 5-and 6-Membered Cyclic Carbonates by Palladium-Catalyzed Oxidative Carbonylation of 1,2-and 1,3-Diols [J].

Gabriele, Bartolo ;

Mancuso, Raffaella ;

Salerno, Giuseppe ;

Veltri, Lucia ;

Costa, Mirco ;

Dibenedetto, Angela .

CHEMSUSCHEM, 2011, 4 (12) :1778-1786

← 1 2 3 4 5 →