Metal-free and Selectfluor-mediated diverse transformations of 2-alkylthiobenzamides to access 2,3-dihydrobenzothiazin-4-ones, benzoisothiazol-3-ones and 2-alkylthiobenzonitriles

被引：0
|
作者：
Dai, Shengfei [1 ]
Yang, Ke [1 ]
Luo, Yanqi [1 ]
Xu, Ziyuan [1 ]
Li, Zhi [1 ]
Li, Zhengyi [1 ]
Li, Bijin [2 ]
Sun, Xiaoqiang [1 ]
机构：
[1] Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Jiangsu, Changzhou,213164, China
[2] Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing,401331, China
来源：
Organic Chemistry Frontiers | 2022年 / 9卷 / 15期
基金：
中国国家自然科学基金;
关键词：
Iodine compounds - Sodium Iodide;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Diverse transformations of 2-alkylthiobenzamides have been established to synthesize 2,3-dihydrobenzothiazin-4-ones, benzoisothiazol-3-ones and 2-alkylthiobenzonitriles in the presence of Selectfluor. Both NaI-HI and TFA-Ac2O systems control the selective C-S bond cleavage and C-H bond functionalization to access 2,3-dihydrobenzothiazin-4-ones and 2-substituted 2,3-dihydrobenzothiazin-4-ones, respectively. Notably, this is the first example of using Selectfluor as a methylene source to construct important 2,3-dihydrobenzothiazin-4-ones. In the presence of HCl, benzoisothiazol-3-ones were obtained in good yields. Furthermore, 2-alkylthiobenzonitriles could also be prepared using the same NaI-HI system via a thioether-directed and Selectfluor-mediated dehydration of 2-alkylthiobenzamides. © 2022 The Royal Society of Chemistry.
引用
收藏
页码：4016 / 4022
相关论文
共 47 条
  • [11] Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation-cyclization cascade mediated by K2S2O8
    Liu, Qiang
    Lu, Weibang
    Xie, Guanqun
    Wang, Xiaoxia
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 1974 - 1982
  • [12] Metal-Free Oxidative C(sp3)-N Coupling by HBr and DMSO: A Novel Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones
    Rezaei, Narjes
    Sheikhi, Ehsan
    Ranjbar, Parviz Rashidi
    SYNLETT, 2018, 29 (07) : 912 - 917
  • [13] Organocatalytic hetero [4+2] cycloaddition reactions of 2-(1-alkynyl)-2-alkene-1-ones: metal-free access to highly substituted 4H-pyrans
    Yu, Xiuzhao
    Cao, Zhongyan
    Zhang, Junliang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (22) : 5059 - 5061
  • [14] Trifluoroacetic Acid-Mediated Denitrogenative ortho-Hydroxylation of 1,2,3-Benzotriazin-4(3H)-ones: A Metal-Free Approach
    Madasamy, Kanagaraj
    Balakrishnan, Madasamy Hari
    Korivi, Ramaraju
    Mannathan, Subramaniyan
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (13): : 8752 - 8756
  • [15] Piperidine-Mediated [3+3] Cyclization of 2-Amino-4H- nchromen-4-ones and 2-Benzylidenemalononitriles: To Access 2-Aminochromeno[2,3-b]pyridine Derivatives
    Zhang, Dan
    Luo, Naili
    Gan, Jianbo
    Wan, Xinyi
    Wang, Cunde
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (13): : 9218 - 9224
  • [16] Metal-free Synthesis of Spiro-2,2′-benzo[b]furan-3,3′-ones via PhI(OAc)2-Mediated Cascade Spirocyclization
    Xing, Qingyu
    Liang, Huiyuan
    Bao, Mingmai
    Li, Xuemin
    Zhang, Jingran
    Bi, Tianhao
    Zhang, Yilin
    Xu, Jun
    Du, Yunfei
    Zhao, Kang
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (20) : 4669 - 4673
  • [17] Metal-free catalyzed oxidative trimerization of indoles by using TEMPO in air: a biomimetic approach to 2-(1H-indol-3-yl)-2,3′-biindolin-3-ones
    Qin, Wen-Bing
    Chang, Qiong
    Bao, Yun-Hong
    Wang, Ning
    Chen, Zheng-Wang
    Liu, Liang-Xian
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (44) : 8814 - 8821
  • [18] Metal-Free Temperature-Controlled Intermolecular [3+2] Annulation to Access Benzo[d]thiazole-2(3H)-thiones and Benzo[d]thiazol-2(3H)-ones
    Zhuo, Xiaoya
    Zheng, Lvyin
    Zou, Xiaoying
    Zhong, Yumei
    Guo, Wei
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (15): : 10467 - 10475
  • [19] Three-component one-pot metal-free synthesis of 2,3-dihydroquinazolin-4(1H)-ones using Mukaiyama's reagent
    Kumar, Ashish
    Gupta, Monika
    Rajput, Chatrasal S.
    ARKIVOC, 2023,
  • [20] Phl(OCOCF3)2-Mediated C-C Bond Formation Concomitant with a 1,2-Aryl Shift in a Metal-Free Synthesis of 3-Arylquinolin-2-ones
    Liu, Le
    Lu, Hang
    Wang, Hong
    Yang, Chao
    Zhang, Xiang
    Zhang-Negrerie, Daisy
    Du, Yunfei
    Zhao, Kang
    ORGANIC LETTERS, 2013, 15 (12) : 2906 - 2909
12345