Diastereoselective Synthesis of 4-Hydroxy-2-quinolinones via Formal [2+4] Cycloaddition Reactions Using α-Diazo Pyrazoleamides as C2 Synthons

被引：0

作者：

Li, Pei ^{[1
]}

Shi, Maoqing ^{[1
]}

Yang, Kaixin ^{[1
]}

Jing, Tongfei ^{[2
]}

Kang, Zhenghui ^{[2
]}

Hu, Wenhao ^{[1
]}

Qian, Yu ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Prov Key Lab Chiral Mol & Drug Discovery, State Key Lab Antiinfect Drug Discovery & Dev, Guangzhou 510006, Peoples R China

[2] Chinese Acad Sci, Zhongshan Inst Drug Discovery, Inst Mat Med, Zhongshan 528400, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 26期

基金：

中国国家自然科学基金;

关键词：

STEREOSELECTIVE-SYNTHESIS; QUINOLONE; COMPLEX; REARRANGEMENT; CYCLIZATION; ALKYNES; YLIDES;

D O I：

10.1021/acs.orglett.4c01956

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rhodium-catalyzed highly stereoselective formal [2 + 4]-cycloaddition reaction of alpha-diazo pyrazoleamides and 2-aminophenyl ketones that produces 4-hydroxy-2-quinolinones in good yields with excellent diastereoselectivities has been developed. A pyrazolium ylide species that is generated from alpha-diazo pyrazoleamides is used as a C2 synthon for this cycloaddition. This protocol offers an efficient approach to a variety of 4-hydroxy-2-quinolinones featuring sequential quaternary centers.

引用

页码：5554 / 5559

页数：6

共 50 条

[1] A review on anticancer potential of bioactive heterocycle quinoline [J].

Afzal, Obaid ;

Kumar, Suresh ;

Haider, Md Rafi ;

Ali, Md Rahmat ;

Kumar, Rajiv ;

Jaggi, Manu ;

Bawa, Sandhya .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 97 :871-910

[2] Cytotoxicity, antioxidant, and antimicrobial activities of novel 2-quinolone derivatives derived from coumarin [J].

Al-Amiery, Ahmed A. ;

Al-Bayati, Redha I. H. ;

Saour, Kawkab Y. ;

Radi, Mahdi F. .

RESEARCH ON CHEMICAL INTERMEDIATES, 2012, 38 (02) :559-569

[3] Diastereoselective synthesis of isochromans via the Cu(ii)-catalysed intramolecular Michael-type trapping of oxonium ylides [J].

Alavala, Gopi Krishna Reddy ;

Sajjad, Farrukh ;

Shi, Taoda ;

Kang, Zhenghui ;

Ma, Mingliang ;

Xing, Dong ;

Hu, Wenhao .

CHEMICAL COMMUNICATIONS, 2018, 54 (89) :12650-12653

[4] Mechanism of Quinolone Action and Resistance [J].

Aldred, Katie J. ;

Kerns, Robert J. ;

Osheroff, Neil .

BIOCHEMISTRY, 2014, 53 (10) :1565-1574

[5] Site- and Enantioselective C-H Oxygenation Catalyzed by a Chiral Manganese Porphyrin Complex with a Remote Binding Site [J].

Burg, Finn ;

Gicquel, Maxime ;

Breitenlechner, Stefan ;

Pothig, Alexander ;

Bach, Thorsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (11) :2953-2957

[6] Cycloaddition reactions of enoldiazo compounds [J].

Cheng, Qing-Qing ;

Deng, Yongming ;

Lankelma, Marianne ;

Doyle, Michael P. .

CHEMICAL SOCIETY REVIEWS, 2017, 46 (17) :5425-5443

[7] Catalytic Asymmetric Halogenation/Semipinacol Rearrangement of 3-Hydroxyl-3-vinyl Oxindoles: A Stereodivergent Kinetic Resolution Process [J].

Dai, Li ;

Liu, Wen ;

Zhou, Yuqiao ;

Zeng, Zi ;

Hu, Xinyue ;

Cao, Weidi ;

Feng, Xiaoming .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (51) :26599-26603

[8] Asymmetric Catalytic Rearrangements with α-Diazocarbonyl Compounds [J].

Dong, Shunxi ;

Liu, Xiaohua ;

Feng, Xiaoming .

ACCOUNTS OF CHEMICAL RESEARCH, 2022, 55 (03) :415-428

[9] Copper-catalyzed C(sp)-H aryl amination enables modular synthesis of quinolines and 2-quinolinones [J].

Gao, Yang ;

Li, Haixia ;

Yang, Simin ;

Huo, Yanping ;

Chen, Qian ;

Li, Xianwei ;

Wang, Zhe ;

Hu, Xiao-Qiang .

SCIENCE CHINA-CHEMISTRY, 2024, 67 (02) :595-603

[10] Catalytic Asymmetric P-H Insertion Reactions [J].

Gu, Xiu ;

Mo, Xiaoyu ;

Bai, Wen-Ju ;

Xie, Peng ;

Hu, Wenhao ;

Jiang, Jun .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (36) :20031-20040

← 1 2 3 4 5 →