Three-component synthesis of N-naphthyl pyrazoles via Rh(iii)-catalyzed cascade pyrazole annulation and Satoh-Miura benzannulation

被引：31

作者：

Chen, Demao ^{[1
]}

Zhou, Liyun ^{[1
]}

Liu, Yunyun ^{[1
]}

Wan, Jie-Ping ^{[1
,2
]}

机构：

[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Natl Engn Res Ctr Carbohydrate Synth, Nanchang 330022, Peoples R China

[2] Nanjing Forestry Univ, Int Innovat Ctr Forest Chem & Mat, Nanjing 210037, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 27期

基金：

中国国家自然科学基金;

关键词：

C-H FUNCTIONALIZATION; III-CATALYZED SYNTHESIS; INTERNAL ALKYNES; DIVERGENT SYNTHESIS; ENAMINONES; ACTIVATION; PHENYLAZOLES; DERIVATIVES; MULTIPLE; CLEAVAGE;

D O I：

10.1039/d3cc00649b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of N-naphthyl pyrazoles has been realized by the direct three-component reactions of enaminones, aryl hydrazine hydrochlorides and internal alkynes via Rh(iii) catalysis. The synthetic reactions employing simple substrates lead to simultaneous construction of dual cyclic moieties, including a pyrazole ring and a phenyl ring, via sequential formation of two C-N and three C-C bonds.

引用

页码：4036 / 4039

页数：4

共 65 条

[1] Metal-Free Multicomponent Strategy for Amidine Synthesis [J].

Alassad, Zayed ;

AboRaed, Anas ;

Mizrachi, Meital Shema ;

Perez-Temprano, Monica H. ;

Milo, Anat .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (45) :20672-20679

[2] Rhodium(II)-catalyzed multicomponent assembly of α,α,α-trisubstituted esters via formal insertion of O-C(sp3)-C(sp2) into C-C bonds [J].

Ba, Dan ;

Wen, Si ;

Tian, Qingyu ;

Chen, Yanhui ;

Lv, Weiwei ;

Cheng, Guolin .

NATURE COMMUNICATIONS, 2020, 11 (01)

[3] Benzannulation strategies for the synthesis of carbazoles, indolocarbazoles, benzocarbazoles, and carbolines [J].

Banerjee, Ankush ;

Kundu, Samrat ;

Bhattacharyya, Arya ;

Sahu, Samrat ;

Maji, Modhu Sudan .

ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (11) :2710-2771

[4] Rh(III)-Catalyzed Weakly Coordinating 2-Pyridone-Directed Oxidative Annulation Using Internal Alkynes: A Reversal in Selectivity [J].

Bera, Satabdi ;

Sarkar, Sanhita ;

Pal, Juthi ;

Samanta, Rajarshi .

ORGANIC LETTERS, 2022, 24 (46) :8470-8475

[5] Weak Directing Group Steered Formal Oxidative [2+2+2]-Cyclization for Selective Benzannulation of Indoles [J].

Bettadapur, Kiran R. ;

Kapanaiah, Raja ;

Lanke, Veeranjaneyulu ;

Prabhu, Kandikere Ramaiah .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (04) :1810-1818

[6] All-Carbon [3+3] Oxidative Annulations of 1,3-Enynes by Rhodium(III)-Catalyzed C-H Functionalization and 1,4-Migration [J].

Burns, David J. ;

Best, Daniel ;

Wieczysty, Martin D. ;

Lam, Hon Wai .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (34) :9958-9962

[7] Nickel-Catalyzed Multicomponent Coupling: Synthesis of α-Chiral Ketones by Reductive Hydrocarbonylation of Alkenes [J].

Chen, Jian ;

Zhu, Shaolin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (35) :14089-14096

[8] Thiazole-5-carbaldehyde Synthesis by Cascade Annulation of Enaminones and KSCN with Dess-Martin Periodinane Reagent [J].

Chen, Kang ;

Zhao, Baoli ;

Liu, Yunyun ;

Wan, Jie-Ping .

JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (21) :14957-14964

[9] Highly Regioselective and Chemoselective [3+3] Annulation of Enaminones with ortho-Fluoronitrobenzenenes: Divergent Synthesis of Aposafranones and Their N-Oxides [J].

Chen, Xue-Bing ;

Huang, Shun-Tao ;

Li, Jie ;

Yang, Qi ;

Yang, Li ;

Yu, Fuchao .

ORGANIC LETTERS, 2021, 23 (08) :3032-3037

[10] Electrochemical Synthesis of Polysubstituted Sulfonated Pyrazoles via Cascade Intermolecular Condensation, Radical-Radical Cross Coupling and Annulation [J].

Feng, Jiajun ;

Wang, Yuzhi ;

Gao, Luoyu ;

Yu, Yang ;

Baell, Jonathan B. ;

Huang, Fei .

JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (19) :13138-13153

← 1 2 3 4 5 6 7 →