Oxidant/Solvent-Controlled I2-Catalyzed Domino Annulation for Selective Synthesis of 2-Aroylbenzothiazoles and 2-Arylbenzothiazoles under Metal-Free Conditions

被引：21
作者：
Ma, Renchao [1 ,2 ]
Ding, Yuxin [1 ,2 ]
Chen, Rener [1 ,2 ]
Wang, Zhiming [1 ,2 ]
Wang, Lei [1 ,2 ]
Ma, Yongmin [1 ,2 ]
机构：
[1] Taizhou Univ, Inst Adv Studies, Taizhou 318000, Peoples R China
[2] Taizhou Univ, Sch Pharmaceut & Chem Engn, Taizhou 318000, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 01期
关键词：
ONE-POT SYNTHESIS; OXIDATIVE SYNTHESIS; 2-SUBSTITUTED BENZIMIDAZOLES; SUBSTITUTED BENZOTHIAZOLES; ARYL KETONES; EFFICIENT; CYCLIZATION; ACCESS; MILD; ACID;
D O I：
10.1021/acs.joc.0c02095
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and practical domino protocol for the selective synthesis of 2-aroylbenzothiazoles and 2-aryl benzothiazoles catalyzed by I-2 is developed under metal-free conditions. The reaction outcomes are exclusively controlled by the reaction oxidant/medium. With DMSO employed as both the solvent and the oxidant, an oxidation of aromatic methyl ketones takes precedence over the condensation with 2-aminobenzenethiols. On the other hand, when the reaction was carried out in PhNO2 or in 1,4-dioxane containing PhNO2, the condensation of aromatic methyl ketones with 2-aminobenzenethiols has priority to form imines which is followed by an oxidation of the methyl group from ketones to afford 2-arylbenzothiazoles as a sole product. The PhNO2/I-2 co-catalytic system is proposed first time.
引用
收藏
页码：310 / 321
页数：12
相关论文
共 68 条
  • [41] Green synthesis and biological evaluation of 6-substituted-2-(2-hydroxy/methoxy phenyl)benzothiazole derivatives as potential antioxidant, antibacterial and antitumor agents
    Racane, Livio
    Pticek, Lucija
    Fajdetic, Glorija
    Tralic-Kulenovic, Vesna
    Klobucar, Marko
    Pavelic, Sandra Kraljevic
    Peric, Mihaela
    Paljetak, Hana Cipcic
    Verbanac, Donatella
    Starcevic, Kristina
    [J]. BIOORGANIC CHEMISTRY, 2020, 95
  • [42] Benzimidazoles from Aryl Alkyl Ketones and 2-Amino Anilines by an Iodine Catalyzed Oxidative C(CO)-C(alkyl) Bond Cleavage
    Ravi, Owk
    Shaikh, Altab
    Upare, Atul
    Singarapu, Kiran Kumar
    Bathula, Surendar Reddy
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (08) : 4422 - 4428
  • [43] An efficient acid- and metal-free one-pot synthesis of benzothiazoles from carboxylic acids
    Rudrawar, S
    Kondaskar, A
    Chakraborti, AK
    [J]. SYNTHESIS-STUTTGART, 2005, (15): : 2521 - 2526
  • [44] Photocatalysis by 3,6-Disubstituted-s-Tetrazine: Visible-Light Driven Metal-Free Green Synthesis of 2-Substituted Benzimidazole and Benzothiazole
    Samanta, Suvendu
    Das, Sudipto
    Biswas, Papu
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (22) : 11184 - 11193
  • [45] Sustainable Catalytic Process with a High Eco-Scale Score for the Synthesis of Five-, Six-, and Seven-Membered Heterocyclic Compounds Using Nanocrystalline Zeolites
    Sarmah, Bhaskar
    Srivastava, Rajendra
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (07) : 873 - 889
  • [46] Lawesson's reagent and microwaves:: A new efficient access to benzoxazoles and benzothiazoles from carboxylic acids under solvent-free conditions
    Seijas, Julio A.
    Vazquez-Tato, A. Pilar
    Carballido-Reboredo, A. Raquel
    Crecente-Campo, Jose
    Romar-Lopez, Lucia
    [J]. SYNLETT, 2007, (02) : 313 - 317
  • [47] Metal-free selective synthesis of 2-substituted benzimidazoles catalyzed by Bronsted acidic ionic liquid: Convenient access to one-pot synthesis of N-alkylated 1,2-disubstituted benzimidazoles
    Senapak, Warapong
    Saeeng, Rungnapha
    Jaratjaroonphong, Jaray
    Promarak, Vinich
    Sirion, Uthaiwan
    [J]. TETRAHEDRON, 2019, 75 (26) : 3543 - 3552
  • [48] Influences of Structural Modification of Naphthalenediimides with Benzothiazole on Organic Field-Effect Transistor and Non-Fullerene Perovskite Solar Cell Characteristics
    Shaikh, Dada B.
    Said, Ahmed Ali
    Wang, Zongrui
    Rao, Pedada Srinivasa
    Bhosale, Rajesh S.
    Mak, Adrian M.
    Zhao, Kexiang
    Zhou, Yu
    Liu, Wenbo
    Gao, Weibo
    Xie, Jian
    Bhosale, Sidhanath V.
    Bhosale, Sheshanath V.
    Zhang, Qichun
    [J]. ACS APPLIED MATERIALS & INTERFACES, 2019, 11 (47) : 44487 - 44500
  • [49] Copper-Catalyzed Oxidative Decarboxylative Arylation of Benzothiazoles with Phenylacetic Acids and α-Hydroxyphenylacetic Acids with O2 as the Sole Oxidant
    Song, Qiuling
    Feng, Qiang
    Zhou, Mingxin
    [J]. ORGANIC LETTERS, 2013, 15 (23) : 5990 - 5993
  • [50] Copper-Catalyzed Synthesis of Substituted Benzothiazoles via Condensation of 2-Aminobenzenethiols with Nitriles
    Sun, Yadong
    Jiang, Huanfeng
    Wu, Wanqing
    Zeng, Wei
    Wu, Xia
    [J]. ORGANIC LETTERS, 2013, 15 (07) : 1598 - 1601
1234567