One-Pot, Borax-mediated synthesis of structurally diverse N, S-heterocycles in water

被引:6
|
作者
Rao, Mugada Sugunakara [1 ]
Hussain, Sahid [1 ]
机构
[1] Indian Inst Technol Patna, Dept Chem, Patna 801106, Bihar, India
关键词
Borax; Quinazolin-4(3H)-one; Benzothiadiazine; 1; 1-Dioxide; Benzothioazole; alpha alpha alpha-Trihalotoluene; CATALYZED DOMINO SYNTHESIS; OXIDATIVE SYNTHESIS; SUBSTITUTED QUINAZOLIN-4(3H)-ONES; MICROWAVE IRRADIATION; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; ANTICANCER AGENTS; MICHAEL REACTIONS; FACILE SYNTHESIS; O-IODOANILINES;
D O I
10.1016/j.tetlet.2021.153159
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, a borax-mediated convenient and efficient strategy for the synthesis of prominent structurally diverse N, S-heterocycles such as quinazolin-4(3H)-one, benzothiadiazine 1,1-dioxide, benzothioazole, and benzoxazoles from readily available 2-aminobenzamide/2-aminobenzenesulfonamide/2-aminothiophenol/2-aminophenol with alpha,alpha,alpha-trihalotoluenes at 100 degrees C in water is elaborated. Upon using aldehydes instead of alpha,alpha,alpha-trihalotoluenes, the reactions proceed through domino fashion under the catalytic effect borax to yield 2,3-dihydroquinazolin-4(1H)-one, 3,4-dihydrothiadiazine 1,1-dioxide, and benzothiazoles in one-pot at 60 degrees C The advantages of this protocol are practical simplicity, large substrate scope, moderate to excellent yields, and the use of water as the solvent. (C) 2021 Elsevier Ltd. All rights reserved.
引用
收藏
页数:7
相关论文
共 50 条
  • [1] One-Pot Synthesis of Five and Six Membered N, O, S-Heterocycles Using a Ditribromide Reagent
    Yella, Ramesh
    Patel, Bhisma K.
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (05): : 754 - 763
  • [2] One-pot synthesis and gelation by borax of glycopolymers in water
    Audebeau, Etienne
    Oikonomou, Evdokia K.
    Norvez, Sophie
    Iliopoulos, Ilias
    POLYMER CHEMISTRY, 2014, 5 (07) : 2273 - 2281
  • [3] One-pot reactions of three-membered rings giving N,O,S-heterocycles
    Palchykov, Vitalii A.
    Zhurakovskyi, Oleksandr
    ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 133, 2021, 133 : 159 - 223
  • [4] One-Pot Synthesis of Structurally Diverse Iminosugar-Based Hybrid Molecules
    Prasad, Sure Siva
    Reddy, Narra Rajashekar
    Baskaran, Sundarababu
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (17): : 9604 - 9618
  • [5] A convenient and expeditious synthesis of annulated N,S-heterocycles
    Saxena, AS
    Goel, A
    Ram, VJ
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2003, 80 (04) : 311 - 318
  • [6] Diacetoxyiodobenzene Mediated One-Pot Synthesis of Diverse Carboxamides from Aldehydes
    Prasad, Virendra
    Kale, Raju R.
    Mishra, Bhuwan B.
    Kumar, Dhananjay
    Tiwari, Vinod K.
    ORGANIC LETTERS, 2012, 14 (12) : 2936 - 2939
  • [7] Synthesis of Structurally Diverse Substituted Aziridinyl Glycoconjugates via Base-Mediated One-Pot Post-Ugi Cyclization
    Sangwan, Rekha
    Dubey, Atul
    Prajapati, Gurudayal
    Arripapathi, Ravi Sankar
    Mandal, Pintu Kumar
    ORGANIC LETTERS, 2019, 21 (08) : 2859 - 2862
  • [8] Highly efficient one-pot synthesis of dihydropyran heterocycles
    Mohamed A.Ameen
    Sara M.Motamed
    Fathy F.Abdel-latif
    Chinese Chemical Letters, 2014, 25 (02) : 212 - 214
  • [9] Highly efficient one-pot synthesis of dihydropyran heterocycles
    Ameen, Mohamed A.
    Motamed, Sara M.
    Abdel-latif, Fathy F.
    CHINESE CHEMICAL LETTERS, 2014, 25 (02) : 212 - 214
  • [10] A versatile approach for one-pot synthesis of hybridized quinolines linked to fused N-containing heterocycles in water
    Rezvanian, Atieh
    Khodadadi, Behnoosh
    Tafreshi, Sepideh
    Shiri, Pezhman
    MOLECULAR DIVERSITY, 2024, 28 (01) : 197 - 207