Visible-Light-Driven One-Pot Synthesis of Benzimidazoles, Benzothiazoles, and Quinazolinones Catalyzed by Scalable and Reusable Ba-Doped CoMoO4 Nanoparticles Under Air Atmosphere

被引:14
作者
Abinaya, Ramanjulu [1 ]
Elavarasan, Selvaraj [1 ]
Binish, B. [2 ]
Rahulan, K. Mani [2 ]
Balasubramanian, Kalpattu K. [3 ]
Manokaran, Kamaraj [4 ]
Varathan, Elumalai [5 ]
Baskar, Baburaj [1 ]
机构
[1] SRM Inst Sci & Technol, Dept Chem, Lab Sustainable Synth, Kattankulatur 603203, Tamilnadu, India
[2] SRM Inst Sci & Technol, Dept Phys & Nanotechnol, Kattankulatur 603203, Tamilnadu, India
[3] Indian Inst Technol, Adjunct Fac, Dept Chem, Chennai 600036, Tamilnadu, India
[4] Univ Manitoba, Dept Chem, Winnipeg, MB, Canada
[5] SRM Inst Sci & Technol, Dept Chem, Kattankulatur 603203, Tamilnadu, India
关键词
benzimidazole; benzothiazole; heterogeneous catalysis; photo-redox catalysis; AEROBIC OXIDATION; HIGHLY EFFICIENT; O-AMINO/MERCAPTAN/HYDROXYANILINES; ANTIBACTERIAL ACTIVITY; BIOLOGICAL EVALUATION; MOLECULAR-OXYGEN; IMINES; AMINES; DERIVATIVES; BINDING;
D O I
10.1002/ejoc.202201098
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein we report a simple and efficient oxidative coupling of various aryl methyl amines with diverse coupling partners, such as o-phenylenediamine (benzene-1,2-diamine), 2-aminobenzenethiol and 2-aminobenzamide, to synthesize the corresponding heterocycles using scalable and reusable heterogeneous catalysts under visible light irradiation. A systematic investigation led to the synthesis of benzimidazoles, benzothiazoles and quinazolinones under air atmosphere in very good to excellent yields. The strategy is atom economical and found to be tolerance towards different functional groups, and wide range of substrate scope. Furthermore, the methodology was demonstrated for its suitability on scale up and reusability. The density functional theory (DFT) calculations and the analysis of band structures of pristine and Ba doped CoMoO4 systems showed that the doping of Ba in place of Co improved the catalytic performance of the system.
引用
收藏
页数:11
相关论文
共 83 条
[1]   Synthesis and pharmacological evaluation of some 3-phenyl-2-substituted-3H-quinazolin-4-one as analgesic, anti-inflammatory agents [J].
Alagarsamy, V. ;
Solomon, V. Raja ;
Dhanabal, K. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (01) :235-241
[2]  
Alamgir M, 2007, TOP HETEROCYCL CHEM, V9, P87, DOI 10.1007/7081_2007_088
[3]   A short synthesis of the PARP inhibitor 2-(4-trifluoromethylphenyl)benzimidazole-4-carboxamide (NU1077) [J].
Austen, SC ;
Kane, JM .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (04) :979-980
[4]   Catalytic performance of a metal-free graphene oxide-Al2O3 composite assembled by 3D printing [J].
Azuaje, Jhonny ;
Rama, Adrian ;
Mallo-Abreu, Ana ;
Boado, Monica G. ;
Majellaro, Maria ;
Tubio, Carmen R. ;
Prieto, Ruben ;
Garcia-Mera, Xerardo ;
Guitian, Francisco ;
Sotelo, Eddy ;
Gil, Alvaro .
JOURNAL OF THE EUROPEAN CERAMIC SOCIETY, 2021, 41 (02) :1399-1406
[5]   A simple and efficient one-pot synthesis of 2-substituted benzimidazoles [J].
Bahrami, Kiumars ;
Khodaei, Mohammad Mehdi ;
Kavianinia, Iman .
SYNTHESIS-STUTTGART, 2007, (04) :547-550
[6]   Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles [J].
Bahrami, Kiumars ;
Khodaei, Mohammad M. ;
Nejati, Akbar .
GREEN CHEMISTRY, 2010, 12 (07) :1237-1241
[7]  
Beaulieu PL, 2003, SYNTHESIS-STUTTGART, P1683
[8]   OXIDATION WITH METAL OXIDES .2. OXIDATION OF CHALCONE PHENYLHYDRAZONES PYRAZOLINES OMICRON-AMINOBENZYLIDINE ANILS AND OMICRON-HYDROXY BENZYLIDINE ANILS WITH MANGANESE DIOXIDE [J].
BHATNAGAR, I ;
GEORGE, MV .
TETRAHEDRON, 1968, 24 (03) :1293-+
[9]   IMPROVED TETRAHEDRON METHOD FOR BRILLOUIN-ZONE INTEGRATIONS [J].
BLOCHL, PE ;
JEPSEN, O ;
ANDERSEN, OK .
PHYSICAL REVIEW B, 1994, 49 (23) :16223-16233
[10]   A rapid and efficient route to benzazole heterocycles [J].
Carpenter, Richard D. ;
Kurth, Mark J. .
NATURE PROTOCOLS, 2010, 5 (11) :1731-1736