Organocatalyzed Formal [4+2] Cycloaddition of in situ Generated Azoalkenes with Arylacetic Acids: An Efficient Approach to the Synthesis of 4,5-Dihydropyridazin-3(2H)-ones

被引:34
|
作者
Li, Xuanyi [1 ,2 ]
Gai, Kuo [1 ,2 ]
Yuan, Zhenbo [1 ,2 ]
Wu, Jie [1 ,2 ]
Lin, Aijun [1 ,2 ]
Yao, Hequan [1 ,2 ]
机构
[1] China Pharmaceut Univ, SKLNM, Nanjing 210009, Peoples R China
[2] China Pharmaceut Univ, Sch Pharm, Dept Med Chem, Nanjing 210009, Peoples R China
基金
中国国家自然科学基金;
关键词
1,2-diaza-1,3-dienes; 4,5-dihydropyridazin-3(2H)-ones; isothiourea catalysis; DYNAMIC KINETIC RESOLUTION; ASYMMETRIC-SYNTHESIS; ACYL; 1,2-DIAZA-1,3-DIENES; BENZOTETRAMISOLE; LACTONIZATION; ANNULATION; ANHYDRIDES; REACTIVITY; INDOLES;
D O I
10.1002/adsc.201500645
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An unprecedented [4+2] cycloaddition of in situ generated azoalkenes with arylacetic acids has been developed under the catalysis of isothiourea. The reaction provided an efficient approach to the synthesis of 4,5-dihydropyridazin-3(2H)-one derivatives in moderate to good yields (up to 95%).
引用
收藏
页码:3479 / 3484
页数:6
相关论文
共 50 条
  • [31] A [3+2] NITRILE OXIDE INTERMOLECULAR CYCLOADDITION APPROACH TO 4,5-DIHYDRO-3(2H)-FURANONE AND 3(2H)-FURANONE RING-SYSTEMS - APPLICATION TO THE FORMAL SYNTHESIS OF (+/-)-ASCOFURANONE AND GEIPARVARIN
    TABRIZI, MA
    BARALDI, PG
    GUARNERI, M
    MANFREDINI, S
    POLLINI, GP
    SIMONI, D
    TETRAHEDRON LETTERS, 1991, 32 (05) : 683 - 686
  • [32] An efficient synthesis of 4,5-dihydro-3(2H)-pyridazinone derivatives
    Toth, G
    Molnar, S
    Tamas, T
    Borbely, I
    SYNTHETIC COMMUNICATIONS, 1997, 27 (20) : 3513 - 3523
  • [33] Synthesis and Anti-tubercular Activity of 6-(4-Chloro/Methyl-phenyl)-4-Arylidene-4,5-dihydropyridazin-3(2H)-one Derivatives Against Mycobacterium tuberculosis
    Asif, Mohammad
    Singh, Anita
    LETTERS IN DRUG DESIGN & DISCOVERY, 2015, 12 (06) : 500 - 504
  • [34] Some reactions with 6-(biphenyl)-4-(5-oxo-1,3-diphenyl-2-pyrazolin-4-yl)-4,5-dihydropyridazin-3-(2H)ones
    Kassab, RR
    Sayed, GH
    Radwan, AM
    Abd El-Azzez, N
    REVUE ROUMAINE DE CHIMIE, 2001, 46 (06) : 649 - 655
  • [35] 4,5-DIHYDRO-1,4-BENZOXAZEPIN-3(2H)-ONES
    DERIEG, ME
    STERNBAC.LH
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1966, 3 (02) : 237 - &
  • [36] Crystal structure, Hirshfeld surface analysis and DFT studies of 6-[(E)-2-(thiophen-2-yl)etnenyl]-4,5-dihydropyridazin-3(2H)-one
    Daoui, Said
    Cinar, Emine Berrin
    El Kalai, Fouad
    Saddik, Rafik
    Dege, Necmi
    Karrouchi, Khalid
    Benchat, Noureddine
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2019, 75 : 1880 - +
  • [37] Thermolysis of 5-azido-4-arylpyridazin-3(2H)-ones:: An efficient and versatile synthesis of pyridazino[4,5-b]indoles
    Haider, Norbert
    Wobus, Andrea
    HETEROCYCLES, 2006, 68 (12) : 2549 - 2561
  • [38] A simple and efficient synthesis of 4-mercapto-6-phenylpyridazin-3(2H)-ones
    Tsolomiti, Georgia
    Tsolomiti, Kyriaki
    Tsolomitis, Athanase
    HETEROCYCLIC COMMUNICATIONS, 2007, 13 (2-3) : 161 - 164
  • [39] Synthesis and antimycobacterial activities of some new N-acylhydrazone and thiosemicarbazide derivatives of 6-methyl-4,5-dihydropyridazin-3(2H)-one
    Tan, Oya Unsal
    Ozadali, Keriman
    Yogeeswari, Perumal
    Sriram, Dharmarajan
    Balkan, Ayla
    MEDICINAL CHEMISTRY RESEARCH, 2012, 21 (09) : 2388 - 2394
  • [40] Synthesis and antimycobacterial activities of some new N-acylhydrazone and thiosemicarbazide derivatives of 6-methyl-4,5-dihydropyridazin-3(2H)-one
    Oya Unsal Tan
    Keriman Ozadali
    Perumal Yogeeswari
    Dharmarajan Sriram
    Ayla Balkan
    Medicinal Chemistry Research, 2012, 21 : 2388 - 2394