Palladium-catalyzed amino group arylation of 1,3-disubstituted 1H-pyrazol-5-amine based on Buchwald-Hartwig reaction

被引：6

作者：

Kucharek, Mateusz ^{[1
]}

Danel, Andrzej ^{[2
]}

机构：

[1] Agr Univ Krakow, Fac Food Technol, Dept Biotechnol & Gen Technol Food, 122 Balicka St, PL-30149 Krakow, Poland

[2] Cracow Univ Technol, Fac Mat Engn & Phys, 1 Podchorazych St, PL-30048 Krakow, Poland

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2021年 / 57卷 / 06期

关键词：

5-N-arylaminopyrazoles; palladium catalyst; arylation; cross coupling; INHIBITORS; DERIVATIVES; PD;

D O I：

10.1007/s10593-021-02961-z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient Pd-catalyzed C-N bond formation for the synthesis of different pyrazole derivatives using XPhos as a ligand and KOH as a base is presented. The developed procedure can be successfully applied for the synthesis of 5-N-aryl-1,3-disubstituted 1H-pyrazol-5-amines. Contrary to previously described procedures, this one proceeds in one step utilizing commercially available aminopyrazoles and aryl halides. Thus, a series of 5-N-aryl-1,3-disubstituted 1H-pyrazol-5-amines were obtained with satisfactory yields under optimized reaction conditions.

引用

页码：633 / 639

页数：7

共 24 条

[1] Correlation of spectroscopically determined ligand donor strength and nucleophilicity of substituted pyrazoles [J].

Bernhammer, Jan Christopher ;

Han Vinh Huynh .

DALTON TRANSACTIONS, 2012, 41 (28) :8600-8608

[2] Selected Copper-Based Reactions for C-N, C-O, C-S, and C-C Bond Formation [J].

Bhunia, Subhajit ;

Pawar, Govind Goroba ;

Kumar, S. Vijay ;

Jiang, Yongwen ;

Ma, Dawei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (51) :16136-16179

[3]

Chaczatrian K, 2003, POL J CHEM, V77, P1141

[4] Synthesis of 5-arylamino-1-arylpyrazoles from 5-aminopyrazoles with arylhalides via CuI catalyzed Ullman coupling reaction [J].

Chang, En-Chivan ;

Chen, Chun-Yen ;

Wang, Li-Ya ;

Huang, Yu-Ying ;

Yeh, Mou-Yung ;

Wong, Fung Fuh .

TETRAHEDRON, 2013, 69 (02) :570-576

[5] INTERFERON INDUCING ACTIVITIES OF DERIVATIVES OF 1,3-DIMETHYL-4-(3-DIMETHYLAMINOPROPYLAMINO)-1H-PYRAZOLO[3,4-B]QUINOLINE AND RELATED COMPOUNDS [J].

CRENSHAW, RR ;

LUKE, GM ;

SIMINOFF, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1976, 19 (02) :262-275

[6] A new regiospecific synthesis method of 1H-pyrazolo[3,4-b] quinoxalines - Potential materials for organic optoelectronic devices, and a revision of an old scheme [J].

Danel, Andrzej ;

Wojtasik, Katarzyna ;

Szlachcic, Pawel ;

Gryl, Marlena ;

Stadnicka, Katarzyna .

TETRAHEDRON, 2017, 73 (34) :5072-5081

[7] Synthesis of novel diarylamino-1,3,5-triazine derivatives as FAK inhibitors with anti-angiogenic activity [J].

Dao, Pascal ;

Jarray, Rafika ;

Le Coq, Johanne ;

Lietha, Daniel ;

Loukaci, Ali ;

Lepelletier, Yves ;

Hadj-Slimane, Reda ;

Garbay, Christiane ;

Raynaud, Francoise ;

Chen, Huixiong .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (16) :4552-4556

[8] One-pot synthesis of 5-(substituted-amino)pyrazoles [J].

Dodd, DS ;

Martinez, RL .

TETRAHEDRON LETTERS, 2004, 45 (22) :4265-4267

[9] Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis [J].

Evano, Gwilherm ;

Blanchard, Nicolas ;

Toumi, Mathieu .

CHEMICAL REVIEWS, 2008, 108 (08) :3054-3131

[10] Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds [J].

Fischer, Carolin ;

Koenig, Burkhard .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 :59-74

← 1 2 3 →