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
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 16-17期
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
  • [1] [4+2] Annulation Reaction of In Situ Generated Azoalkenes with Azlactones: Access to 4,5-Dihydropyridazin-3(2H)-Ones
    Yuan, Wei-Cheng
    Quan, Bao-Xue
    Zhao, Jian-Qiang
    You, Yong
    Wang, Zhen-Hua
    Zhou, Ming-Qiang
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (18): : 11812 - 11821
  • [2] PREPARATION AND SOME REACTIONS OF 4-ARYL-4,5-DIHYDROPYRIDAZIN-3(2H)-ONES AND 5-ARYL-4,5-DIHYDROPYRIDAZIN-3(2H)-ONES
    BREUKELMAN, SP
    MEAKINS, GD
    ROE, AM
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (08): : 1627 - 1635
  • [3] A convenient synthesis of new phosphonomethyl-containing 4,5-dihydropyridazin-3(2H)-ones
    Bejaoui, Oumayma
    Abdelli, Abderrahmen
    M'rabet, Hedi
    Moreau, Xavier
    Efrit, Mohamed Lotfi
    Prim, Damien
    MENDELEEV COMMUNICATIONS, 2023, 33 (05) : 640 - 641
  • [4] A new approach to the synthesis of 4-(N-aryl)carbamoylmethyl-4,5-dihydropyridazin-3(2H)-ones
    Stepakov, Alexander V.
    Kinzhalov, Michail A.
    Boitsov, Vitaly M.
    Stepakova, Liubov V.
    Starova, Galina L.
    Vyazmin, Sergey Yu.
    Grinenko, Elena V.
    TETRAHEDRON LETTERS, 2011, 52 (24) : 3146 - 3149
  • [5] Efficient 1,3,4-Thiadiazole-4,5-dihydropyridazin-3(2H)-ones as Antimicrobial Agents
    El-Badry, Yaser Abdel-Moemen
    Sallam, Mohammed Shafie
    El-Hashash, Mahr Abdel-Aziz
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2018, 66 (04) : 427 - 433
  • [6] SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF 4-CARBAMOYL-5-ARYL-6-METHYL-4,5-DIHYDROPYRIDAZIN-3(2H)-ONES
    PINNA, GA
    SARDU, F
    CURZU, MM
    SATTA, M
    PEANA, A
    CIGNARELLA, G
    BARLOCCO, D
    FARMACO, 1992, 47 (04): : 449 - 463
  • [7] Expedient method for the solid-phase synthesis of some 4-substituted-4,5-dihydropyridazin-3(2H)-ones
    Gouault, N
    Cupif, JF
    Amoros, M
    David, M
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (20): : 2234 - 2236
  • [8] Assembly of Dihydropyridazines via [4+2] Cycloaddition of In Situ Generated Azoalkenes
    Yuan, Cheng
    Wang, Jiatong
    Wang, Gangqiang
    Sun, Shaofa
    Wang, Jian
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (02)
  • [9] Synthesis and evaluation of 2-substituted-6-phenyl-4,5-dihydropyridazin-3(2H)-ones as potent inodilators
    Kumar, Dinesh
    Carron, Rosalia
    De la Calle, Carmen
    Jindal, Dharam Paul
    Bansal, Ranju
    ACTA PHARMACEUTICA, 2008, 58 (04) : 393 - 405
  • [10] Synthesis of Perfluoroalkyl-Substituted γ-Lactones and 4,5-Dihydropyridazin-3(2H)-ones via Donor-Acceptor Cyclopropanes
    Gladow, Daniel
    Reissig, Hans-Ulrich
    HELVETICA CHIMICA ACTA, 2012, 95 (10) : 1818 - 1830
12345