Practical Synthesis of Functionalized Chromeno[3,4-c]pyridine Derivatives via a CuCl2-Catalyzed Tandem Reaction of the Blaise Reaction Intermediates and 3-Cyanocoumarins

被引：4
|
作者：
Fan, Yangyang [1 ]
Zheng, Lei [1 ]
Yang, Zhaohai [1 ]
Li, Jian-Jun [1 ,2 ]
Chen, Zhiwei [1 ,2 ]
机构：
[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, Collaborat Innovat Ctr Yangtze River Delta Reg Gr, Hangzhou 310014, Zhejiang, Peoples R China
来源：
SYNLETT | 2018年 / 29卷 / 07期
基金：
中国国家自然科学基金;
关键词：
tandem reaction; CuCl2-catalyzed; Blaise reaction intermediates; 3-cyanocoumarins; chromeno[3,4-c]pyridines; ONE-POT SYNTHESIS; POLYSUBSTITUTED PYRIDINES; MULTICOMPONENT SYNTHESIS; BIOLOGICAL-ACTIVITY; ANTITUMOR AGENTS; COUMARINS; CYCLIZATION;
D O I：
10.1055/s-0036-1591535
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This work discloses a novel and efficient protocol for the construction of functionalized chromeno[3,4-c]pyridine derivatives from the Blaise reaction intermediates and 3-cyanocoumarins through a CuCl2-catalyzed sequential Michael addition/intramolecular cyclization/oxidative aromatization reaction. This new method shows the advantages of mild reaction conditions, easy workup, nonchromato-graphic purification technique, good functional group tolerance, and moderate to good yields.
引用
收藏
页码：959 / 963
页数：5
相关论文
共 50 条
  • [31] A Facile Synthesis of Furo[3,4-e]pyrazolo[3,4-b]pyridine-5(7H)-one Derivatives via Three-Component Reaction in Ionic Liquid without Any Catalyst
    Shi, Da-Qing
    Yang, Fang
    Ni, Sai-Nan
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (03) : 469 - 476
  • [32] Efficient, Green, Solvent-Free Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones via Biginelli Reaction Catalyzed by Cu(NO3)2•3H2O
    Wang, Dong-Chao
    Guo, Hai-Ming
    Qu, Gui-Rong
    SYNTHETIC COMMUNICATIONS, 2010, 40 (08) : 1115 - 1122
  • [33] Aqueous C-S cross-coupling: synthesis of 2-iminobenzo-1,3-oxathioles via CuCl2•H2O-catalyzed tandem reaction of 2-iodophenols with isothiocyanates
    Ding, Qiuping
    Liu, Xianjin
    Cao, Banpeng
    Zong, Zhenzhen
    Peng, Yiyuan
    TETRAHEDRON LETTERS, 2011, 52 (16) : 1964 - 1967
  • [34] Three-component reaction between substituted 2-(2-nitrovinyl)-phenols, acetylenedicarboxylate and amines: diversity-oriented synthesis of novel pyrrolo[3,4-c]coumarins
    Xue, Shuwen
    Yao, Juan
    Liu, Jiaming
    Wang, Lizhong
    Liu, Xinyu
    Wang, Cunde
    RSC ADVANCES, 2016, 6 (03): : 1700 - 1704
  • [35] Selective Synthesis of Functionalized 3(2H)-Furanones via Tandem Michael Addition/Rearrangement/Cyclization Reaction of Aliphatic Alkynones: A Combined Experimental and Theoretical Study
    Karnakova, Sofia O.
    Kuzmin, Anton V.
    Ushakov, Igor' A.
    Shabalin, Dmitrii A.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (17)
  • [36] A simple and efficient synthesis of 3,4-dihydropyrimidin-2-(1H)-ones via Biginelli reaction catalyzed by nanomagnetic-supported sulfonic acid
    Kolvari, Eskandar
    Koukabi, Nadiya
    Armandpour, Ozra
    TETRAHEDRON, 2014, 70 (06) : 1383 - 1386
  • [37] g-C3N4/Fe2O3/ZIF-8 catalyst for the synthesis of polyhydroquinoline derivatives via Hantzsch reaction
    Ghiaci, Zahra Golami
    Rafiee, Zahra
    RESEARCH ON CHEMICAL INTERMEDIATES, 2024, 50 (03) : 1161 - 1175
  • [38] Practical Stereoselective Synthesis of C3-Spirooxindole- and C2-Spiropseudoindoxyl-Pyrrolidines via Organocatalyzed Pictet-Spengler Reaction/Oxidative Rearrangement Sequence
    Kondo, Masaru
    Matsuyama, Naoki
    Aye, Tin Z.
    Mattan, Irshad
    Sato, Tomoyuki
    Makita, Yoshinori
    Ishibashi, Masami
    Arai, Midori A.
    Takizawa, Shinobu
    Sasai, Hiroaki
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (10) : 2648 - 2663
  • [39] Synthesis of pyrano[3,2-c]quinolones and furo[3,2-c]quinolones via acid-catalyzed tandem reaction of 4-hydroxy-1-methylquinolin-2(1H)-one and propargylic alcohols
    Yin, Haiting
    Wu, Yunjun
    Gu, Xiaoxia
    Feng, Zhijun
    Wang, Meifang
    Feng, Dexiang
    Wang, Ming
    Cheng, Ziyang
    Wang, Shaoyin
    RSC ADVANCES, 2022, 12 (33) : 21066 - 21078
  • [40] An Efficient Five-Component Reaction for the Synthesis of 4,4′-((2-Oxoindoline-3,3-diyl)bis(methylene))bis(2-aryl-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione) Derivatives
    Mao, Kaimin
    Dai, Lei
    Liu, Yun
    Rong, Liangce
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (08) : 2111 - 2120
12345