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
  • [1] Four component synthesis of pyrrolo[3,2-c]pyridin-4-one derivatives
    Li, Chunmei
    Fan, Weiming
    Qi, Chenze
    Zhang, Furen
    TETRAHEDRON LETTERS, 2020, 61 (34)
  • [2] Vilsmeier-Type Reaction of Dimethylaminoalkenoyl Cyclopropanes: One-Pot Access to 2,3-Dihydrofuro [3,2-c]pyridin-4(5H)-ones
    Huang, Peng
    Zhang, Ning
    Zhang, Rui
    Dong, Dewen
    ORGANIC LETTERS, 2012, 14 (01) : 370 - 373
  • [3] An Efficient Synthesis of 3H-Pyrrolo[3,2-d]pyrimidin-4(5H)-one Derivatives via an Iminophosphorane
    He, Ping
    Yan, Yan-Mei
    Ding, Ming-Wu
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 : E93 - E97
  • [4] Synthesis of methyl derivatives of 4H-furo[2,3-h]quinolin-4-one and 5H-furo[3,2-g]quinolin-5-one
    Rao, VS
    Rodighiero, P
    Chilin, A
    Castellin, A
    Manzini, P
    Guiotto, A
    LIEBIGS ANNALEN-RECUEIL, 1997, (02): : 419 - 422
  • [5] 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
  • [6] Intramolecular-Prins-cyclization: a novel synthesis of hexahydro-2H-furo[3,2-c]pyran derivatives
    Yadav, J. S.
    Chakravarthy, P. Pawan
    Borkar, Prashant
    Reddy, B. V. Subbal
    Sarma, A. V. S.
    TETRAHEDRON LETTERS, 2009, 50 (44) : 5998 - 6000
  • [7] One-pot and step-wise synthesis of thieno[3,2-c] pyridin-4-ones
    Sahu, Satya Narayan
    Singh, Surjeet
    Shaw, Ranjay
    Shally
    Ram, Vishnu Ji
    Pratap, Ramendra
    RSC ADVANCES, 2016, 6 (88): : 85515 - 85520
  • [8] 2H-Azirines as C-C Annulation Reagents in Cu-Catalyzed Synthesis of Furo[3,2-c]quinolone Derivatives
    Sakharov, Pavel A.
    Rostovskii, Nikolai V.
    Khlebnikov, Alexander F.
    Panikorovskii, Taras L.
    Novikov, Mikhail S.
    ORGANIC LETTERS, 2019, 21 (10) : 3615 - 3619
  • [9] Gold-Catalyzed Cascade Reactions of 4H-Furo[3,2-b]indoles with Allenamides: Synthesis of Indolin-3-one Derivatives
    Pirovano, Valentina
    Brarnbilla, Elisa
    Rizzato, Silvia
    Abbiati, Giorgio
    Bozzi, Marta
    Rossi, Elisabetta
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (09) : 5150 - 5166
  • [10] Synthesis of 3-phenyl-2H,5H-pyrano[3,2-c]chromen-2-one derivatives and their antineoplastic activity
    Kovacikova, Lucia
    Gasparova, Renata
    Bohac, Andrej
    Durana, Marian
    Lacova, Margita
    ARKIVOC, 2010, : 188 - 203