Copper-Catalyzed [3+2] Annulation of O-Acyl Oximes with 4-Sulfonamidophenols for the Synthesis of 5-Sulfonamidoindoles and 2-Amido-5-sulfonamidobenzofuran-3(2H)-ones

被引:0
|
作者
Hu, Zi-Jun [1 ]
Chen, Wei [2 ]
Lyu, Xinyu [1 ]
Zhang, Hui-Peng [1 ]
Chen, Si-Wei [1 ]
Ding, Xian-Heng [1 ]
Yu, Cang-Hai [1 ]
Cui, Zhen [1 ]
Miao, Chun-Bao [1 ]
Yang, Hai-Tao [1 ]
机构
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Jiangsu, Peoples R China
[2] Changzhou Siyao Pharmaceut Co Ltd, Changzhou 213018, Jiangsu, Peoples R China
关键词
INDOLES; ACID;
D O I
10.1021/acs.orglett.4c01071
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper-catalyzed [3 + 2] annulation of O-acyl oximes with 4-sulfonamidophenols is developed. The advantage of this method lies in the concurrent double activation of two substrates to form nucleophilic enamines and electrophilic quinone monoimines. The substituent on the alpha-carbon of O-acyl oxime determines two different reaction pathways, thereby leading to the selective generation of 5-sulfonamidoindoles and 2-amido-5-sulfonamidobenzofuran-3(2H)-ones.
引用
收藏
页码:4229 / 4234
页数:6
相关论文
共 50 条
  • [41] Rearrangement of 5-benzoyl-3(2H)-isothiazol-3-ones to 6-benzoyl 2,3-dihydro-1,3-thiazin-4(2H)-ones
    Tsolomiti, Georgia
    Tsolomiti, Kyriaki
    Tsolomitis, Athanase
    [J]. HETEROCYCLIC COMMUNICATIONS, 2006, 12 (3-4) : 247 - 252
  • [42] An efficient synthesis of novel 3′-substituted 2-aryl-5-methyl-5′thioxo-[4,4′-bi-4H-1,2,4-triazol]-3(1′H, 2H)-ones
    Kamble, Ravindra R.
    Sudha, Belgur S.
    [J]. JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2006, 71 (04) : 331 - 337
  • [43] Copper-catalyzed efficient synthesis of 5-arylindazolo[3,2-b]quinazolin-7(5H)-ones from 2-nitrobenzaldehydes
    Fard, Zahra Arasteh
    Dilmaghani, Karim Akbari
    Soheilizad, Mehdi
    Larijani, Bagher
    Mahdavi, Mohammad
    [J]. TETRAHEDRON, 2018, 74 (18) : 2197 - 2201
  • [44] 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
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (08): : 1627 - 1635
  • [45] SYNTHESIS AND PHARMACOLOGICAL STUDY OF 5-ARYL-6-METHYL-4,5-DIHYDRO-PYRIDAZIN-3(2H)ONES AND RELATED 5-ARYL-6-METHYL-PYRIDAZIN-3(2H)ONES
    PINNA, GA
    CURZU, MM
    BARLOCCO, D
    CIGNARELLA, G
    CAVALLETTI, E
    GERMINI, M
    BERGER, K
    [J]. FARMACO-EDIZIONE SCIENTIFICA, 1988, 43 (06): : 539 - 549
  • [46] Copper-Catalyzed Domino-Double Annulation of o-Aminobenzamides with 2-Iodoisothiocyanates for the Synthesis of 12H-Benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones
    Wu, Yingying
    Yang, Beining
    Wang, Yatang
    Zhang, Zhiying
    Li, Yinyin
    Hua, Xiaofeng
    Zheng, Lvyin
    Guo, Wei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (07): : 4774 - 4783
  • [47] Synthesis of 5-Aryl-4-acyl-3-hydroxy-1-(2-furylmethyl)-3-pyrrolin-2-ones
    Gein, V. L.
    Nosova, N. V.
    Shishkin, A. P.
    Gein, L. F.
    [J]. RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2018, 88 (03) : 598 - 601
  • [48] Synthesis of 5-Aryl-4-acyl-3-hydroxy-1-(2-furylmethyl)-3-pyrrolin-2-ones
    V. L. Gein
    N. V. Nosova
    A. P. Shishkin
    L. F. Gein
    [J]. Russian Journal of General Chemistry, 2018, 88 : 598 - 601
  • [49] Synthesis of 4-aryl-1,2,3(1H,2H)-triazolin-5-ones from α-keto acids
    Lakhan, R
    Sharma, BP
    [J]. INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 11 (03) : 191 - 194
  • [50] An efficient approach to construct benzisothiazol-3(2H)-ones via copper-catalyzed consecutive reaction of 2-halobenzamides and carbon disulfide
    Li, Ting
    Yang, Lei
    Ni, Kaidong
    Shi, Zhenyu
    Li, Fei
    Chen, Dongyin
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (26) : 6297 - 6303