An efficient strategy for synthesis of new functionalized furo[3,2-c]pyridin-4(5H)-one derivatives under mild conditions

被引:4
作者
Tao, Jiahao [1 ]
Li, Chunmei [1 ,2 ]
Zhou, Kaini [1 ]
Huan, Yongcan [1 ]
Yuan, Yongjie [1 ]
Liu, Ali [1 ]
Zhang, Furen [1 ]
Qi, Chenze [1 ]
Shen, Zhenlu [2 ]
机构
[1] Shaoxing Univ, Sch Chem & Chem Engn, Zhejiang Key Lab Alternat Technol Fine Chem Proc, Shaoxing 312000, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310032, Peoples R China
基金
中国国家自然科学基金;
关键词
NF-KAPPA-B; IRIDIUM COMPLEXES; CASCADE REACTIONS; FACILE SYNTHESIS; NITROOLEFINS; FUROQUINOLINONES; PHOSPHORESCENT; REARRANGEMENT; CONSTRUCTION; CYCLIZATION;
D O I
10.1002/jhet.4502
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this study, we prepared a series of 5-alkyl-2,6-dimethyl-3-arylfuro[3,2-c]pyridin-4(5H)-one derivatives via the reaction of 1-substitued 4-hydroxy-6-methylpyridin-2(1H)-ones with various nitrostyrenes using triethylamine as catalyst. This strategy not only provided various new 5-alkyl-2,6-dimethyl-3-arylfuro[3,2-c]pyridin-4(5H)-ones, but also expanded the scope of application of active intermediate nitrostyrenes. Meanwhile, this method has the advantages of inexpensive and easily available starting materials, step economy, metal-free catalytic system, good to excellent yields and operational simplicity. A total of 22 heterocyclic compounds were obtained to exhibit a broad substrate scope of the strategy.
引用
收藏
页码:1742 / 1751
页数:10
相关论文
共 50 条
[41]   Copper(I)-mediated preparation of new pyrano[3′,4′:4,5]imidazo[1,2-a]pyridin-1-one compounds under mild palladium-free conditions [J].
Bahlaouan, Zineb ;
Abarbri, Mohamed ;
Duchene, Alain ;
Thibonnet, Jerome ;
Henry, Nicolas ;
Enguehard-Gueiffier, Cecile ;
Gueiffier, Alain .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (04) :1212-1218
[42]   One-Pot Two-Step Strategy for Efficient Synthesis of 3-Aryl-4-(arylthio)-1H-pyrazol-5-amines Derivatives [J].
Feng Yijiao ;
He Jing ;
Wei Yueting ;
Tang Ting ;
Li Chuntian ;
Liu Ping .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (01) :226-234
[43]   Efficient Synthesis of 7H-Chromeno[3,2-c]quinolin-5-ium Salts and Quinolin-4-ones through Acid-Promoted Cascade Reaction of 3-Formylchromones and Anilines [J].
Zhang, Zhong-Wei ;
Liu, Yue-Ying ;
Wang, Si-Yu ;
Zhang, Cong-Hai ;
Lin, Jun .
CHEMISTRYSELECT, 2022, 7 (07)
[45]   Palladium-Catalyzed Chemo- and Regiocontrolled Tandem Cyclization/Cross-Coupling of 2-Benzyl-3-alkynyl Chromones with Aryl Iodides for the Synthesis of 4H-Furo[3,2-c]chromenes and Xanthones [J].
Liang, Yi-En ;
Kan, Chih-Yu ;
Barve, Balaji D. ;
Chen, Yen-An ;
Li, Wen-Tai .
ORGANIC LETTERS, 2022, 24 (37) :6728-6733
[46]   Reaction of 2-alkylthio-6-amino-pyrimidin-4(3H)-ones with ethyl bromopyruvate. Synthesis of furo-[2,3-d]-pyrimidine and furo[3,2-e]imidazo-[1,2-c]pyrimidine carboxylates [J].
Masevicius, V. ;
Petraityte, G. ;
Tumkevicius, S. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (03) :357-360
[47]   Synthesis and structure of a new heterocyclic system: pyrido [3′,2′:4,5]furo[3,2-d][1,2,4]triazolo[4,3-a]pyrimidin-7(8)-one [J].
Sirakanyan, Samvel N. ;
Spinelli, Domenico ;
Geronikaki, Athina ;
Kartsev, Viktor G. ;
Hakobyan, Elmira K. ;
Hovakimyan, Anush A. .
TETRAHEDRON LETTERS, 2016, 57 (48) :5338-5340
[48]   An Efficient and Facile Synthesis of 5-Amino-3-methyl-7-aryl-1,3-dihydroisobenzofuran-4,6-dicarbonitrile Derivatives Under Mild Conditions [J].
Yin, Zehan ;
Wang, Zhansheng ;
Xu, Jing ;
Hao, Ganlu ;
Gao, Xu ;
Rong, Liangce .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (02) :1261-1266
[49]   Facile Synthesis of (2-Amino-3-(benzothiazol-2-yl)-4H-chromen-4-yl)phosphonate Derivatives under Mild Conditions [J].
Yan, Haohao ;
Zhao, Boling ;
Gao, Yu ;
Du, Daming .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (07) :1643-1652
[50]   Reaction of 2-alkylthio-6-amino-pyrimidin-4(3H)-ones with ethyl bromopyruvate. Synthesis of furo-[2,3-d]-pyrimidine and furo[3,2-e]imidazo-[1,2-c]pyrimidine carboxylates [J].
V. Masevicius ;
G. Petraityte ;
S. Tumkevicius .
Chemistry of Heterocyclic Compounds, 2009, 45 :357-360