Iron-Catalyzed Synthesis of Benzosultams from N-Phenyl-N-(prop-2-yn-1-yl)benzenesulfonamide and Benzenesulfonyl Hydrazine

被引:8
作者
Zhang, Mei [1 ]
Yu, Xiao [1 ]
Zhu, Wenjing [1 ]
Liu, Yi [1 ]
Zhang, Zenghui [1 ]
Zhao, Jinbo [1 ]
Xia, Chengcai [1 ]
Li, Ke [1 ]
机构
[1] Shandong First Med Univ & Shandong Acad Med Sci, Inst Pharmacol, Pharm Coll, Tai An 271016, Peoples R China
关键词
D O I
10.1021/acs.orglett.2c04134
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel route for an iron-catalyzed tandem sulfonylation, C(sp2)-H activation, cyclization reaction which uses N-phenyl-N-(prop-2-yn-1-yl)benzenesulfonamide and benzenesulfonohydrazide to synthesize derivatives of (Z)-2-phenyl-4-((phenylsulfonyl)methylene)-3,4-dihydro-2H-benzo[e][1,2]thiazine 1,1-dioxide has been developed. The method features convenient operation and good functional group tolerance. In addition, it employs insensitive and inexpensive FeSO4 as the catalyst and provides a direct approach for the preparation of benzothiazides.
引用
收藏
页码:603 / 607
页数:5
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共 19 条
[1]   Radioiodination, purification and bioevaluation of Piroxicam in comparison with Meloxicam for imaging of inflammation [J].
Amin, A. M. ;
Gouda, A. A. ;
El-Sheikh, R. ;
Seddik, U. ;
Hussien, H. .
JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY, 2009, 280 (03) :589-598
[2]   LIGAND FREE Pd CATALYZED CYCLIZATION-INFLUENCE OF STERIC HINDRANCE [J].
Arshad, Muhammad Nadeem ;
Siddiqui, Waseeq Ahmad ;
Khan, Islam Ullah ;
Asiri, Abdullah M. .
JOURNAL OF THE CHILEAN CHEMICAL SOCIETY, 2014, 59 (04) :2697-2700
[3]   Synthesis and anti-HIV-1 activity of a novel series of 1,4,2-benzodithiazine-dioxides [J].
Brzozowski, Zdzislaw ;
Saczewski, Franciszek ;
Neamati, Nouri .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (20) :5298-5302
[4]   Regio- and Stereoselective Synthesis of Benzo--sultams by Palladium-Catalyzed Hydrocarbonation of Alkynes [J].
Debnath, Sudarshan ;
Mondal, Shovan .
SYNTHESIS-STUTTGART, 2016, 48 (05) :710-722
[5]   Tandem C-C/C-N Formation via Palladium-Catalyzed C-H Activation/Styrenation and Sequential Annulation of O-Methylketoxime with Styrenes [J].
Fu, Xiaopan ;
Yang, Jinyue ;
Deng, Kezuan ;
Shao, Lingyan ;
Xia, Chengcai ;
Ji, Yafei .
ORGANIC LETTERS, 2019, 21 (10) :3505-3509
[6]   Iron-Catalyzed Regioselective Alkoxycarbonylation of Imidazoheterocycles with Carbazates [J].
Gao, Yongyuan ;
Lu, Weiye ;
Liu, Ping ;
Sun, Peipei .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (06) :2482-2487
[7]   Cascade reaction to 1H-pyrazoles from hydrazonesvia sodium ni-trite promoted dual C-C/C-N formation, annulation and aromatization with 1,2-dichloroethane [J].
Hao, Liqiang ;
Liu, Hongyan ;
Zhang, Zheng ;
Wen, Fuqiang ;
Xia, Chengcai ;
Pang, Zengfen .
CHINESE CHEMICAL LETTERS, 2021, 32 (07) :2309-2312
[8]   Structural aspects of isozyme selectivity in the binding of inhibitors to carbonic anhydrases II and IV [J].
Kim, CY ;
Whittington, DA ;
Chang, JS ;
Liao, J ;
May, JA ;
Christianson, DW .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (04) :888-893
[9]   Base-Mediated Coupling Reactions of Benzenesulfonyl Azides with Proline: Synthesis of Proline-Derived Benzenesulfonamides [J].
Liu, Hongyan ;
Zhang, Bin ;
Zhao, Wei ;
Yu, Xiao ;
Zhu, Wenjing ;
Xia, Chengcai ;
Zhou, Yanmeng .
ACS OMEGA, 2021, 6 (50) :34796-34804
[10]   Sulfonylimination of Proline with Sulfonylazides Involving Aldehyde-Induced Decarboxylation Coupling [J].
Liu, Hongyan ;
Pang, Zengfen ;
Hao, Liqiang ;
Sun, Jian ;
Zhang, Zheng ;
Wen, Fuqiang ;
Xia, Chengcai .
ORGANIC LETTERS, 2021, 23 (04) :1234-1238