Gold-Catalyzed Three-Component Annulation: Efficient Synthesis of Highly Functionalized Dihydropyrazoles from Alkynes, Hydrazines, and Aldehydes or Ketones

被引：66

作者：

Suzuki, Yamato ^{[1
]}

Naoe, Saori ^{[1
]}

Oishi, Shinya ^{[1
]}

Fujii, Nobutaka ^{[1
]}

Ohno, Hiroaki ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 01期

关键词：

ONE-POT; FACILE SYNTHESIS; AMINES; ACCESS; CYCLIZATION; PYRAZOLES; HYDROAMINATION; ADDITIONS; BONDS;

D O I：

10.1021/ol203072u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polysubstituted dihydropyrazoles were directly obtained by a gold-catalyzed three-component annulation. This reaction consists of a Mannich-type coupling of alkynes with N,N-disubstituted hydrazines and aldehydes/ketones followed by intramolecular hydroamination. Cascade cyclization using 1,2-dialkynylbenzene derivatives as the alkyne component was also performed producing fused tricyclic dihydropyrazoles in good yields.

引用

页码：326 / 329

页数：4

共 50 条

[41] Gold-Catalyzed Homogeneous Oxidative C-O Bond Formation: Efficient Synthesis of 1-Benzoxyvinyl Ketones [J].

Peng, Yu ;

Cui, Li ;

Zhang, Guozhu ;

Zhang, Liming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (14) :5062-+

[42] Synthesis of 1,3,5-trisubstituted 1,2,4-triazoles enabled by a gold-catalyzed three-component reaction [J].

Diaz-Salazar, Howard ;

Ramirez-Gonzalez, Carlos M. ;

Rosas-Ortega, Miguel A. ;

Porcel, Susana .

TETRAHEDRON, 2024, 168

[43] An efficient and facile one-pot synthesis of propargylamines by three-component coupling of aldehydes, amines, and alkynes via C-H activation catalyzed by NiCl2 [J].

Samai, Subhasis ;

Nandi, Ganesh Chandra ;

Singh, M. S. .

TETRAHEDRON LETTERS, 2010, 51 (42) :5555-5558

[44] One-pot synthesis of 2,4-disubstituted quinolines via silver-catalyzed three-component cascade annulation of amines, alkyne esters and terminal alkynes [J].

Li, Yunlan ;

Zhang, Qiurui ;

Xu, Xuefeng ;

Zhang, Xu ;

Yang, Yurong ;

Yi, Wei .

TETRAHEDRON LETTERS, 2019, 60 (14) :965-970

[45] Squaric Acid Catalyzed Highly Efficient Three-Component Mannich-Type Reaction [J].

Azizi, Najmadin ;

Davoudpour, Anahita .

CATALYSIS LETTERS, 2011, 141 (10) :1506-1510

[46] TBAI-Catalyzed, TBHP-Mediated Modular Three-Component Cascade Towards Highly Functionalized Pyrrole via [3+2] Annulation [J].

Gnanaoli, Karthiyayini ;

Rajkumar, Deepan Babu ;

Gopal, Keerthana ;

Saritha, B. ;

Maheswari, C. Uma .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (20)

[47] Gold-Catalyzed Oxidation/C-H Functionalization of Ynones: Efficient and Rapid Access to Functionalized Polycyclic Salicyl Ketones [J].

Ji, Kegong ;

Yang, Fang ;

Gao, Shiyue ;

Tang, Jiangjiang ;

Gao, Jinming .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (29) :10225-10229

[48] Highly efficient three-component coupling reaction catalyzed by gold nanoparticles supported on periodic mesoporous organosilica with ionic liquid framework [J].

Karimi, Babak ;

Gholinejad, Mohammad ;

Khorasani, Mojtaba .

CHEMICAL COMMUNICATIONS, 2012, 48 (71) :8961-8963

[49] Gold-catalyzed dual annulation of azide-tethered alkynes with nitriles: expeditious synthesis of oxazolo[4,5-c]quinolines [J].

Su, Han ;

Bao, Ming ;

Pei, Chao ;

Hu, Wenhao ;

Qiu, Lihua ;

Xu, Xinfang .

ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (14) :2404-2409

[50] Gold-Catalyzed Tandem Cyclization/Cycloaddition Reaction of Enynones: Highly Regioselective Synthesis of Oxabicyclic Compounds and Naphthyl Ketones [J].

Song, Xian-Rong ;

Xia, Xiao-Feng ;

Song, Bo ;

Tian, Xiang ;

Zhu, Hai-Tiao ;

Zhou, An-Xi ;

Liu, Xue-Yuan ;

Liang, Yong-Min .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2 (09) :755-762

← 1 2 3 4 5 →