Diversity-oriented synthesis of benzimidazole, benzoxazole, benzothiazole and quinazolin-4(3H)-one libraries via potassium persulfate-CuSO4-mediated oxidative coupling reactions of aldehydes in aqueous micelles

被引:35
|
作者
Kumar, Atul [1 ]
Maurya, Ram Awatar [1 ]
Saxena, Deepti [1 ]
机构
[1] Cent Drug Res Inst, Med & Proc Chem Div, Lucknow 226001, Uttar Pradesh, India
关键词
Benzimidazoles; Benzoxazoles; Benzothiazoles; Quinazolin-4(3H)-ones; Potassium persulfate-CuSO4; Oxidative coupling reactions; SCHIFFS BASES; PEROXYDISULFATE; DERIVATIVES; POTENT; CYCLIZATION; ANTAGONISTS; CONVERSION; MECHANISM; CARBONYL; DESIGN;
D O I
10.1007/s11030-009-9170-8
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Libraries of 2-substituted-benzimidazoles, benzoxazoles, benzothiazoles as well as quinazolin-4(3H)-ones were synthesized via potassium persulfate-CuSO4-mediated oxidative coupling of aldehydes with o-phenylenediamines, o-aminophenols, o-aminothiophenols, and anthranilamide, respectively, in aqueous micelles. The strategy opens a way for rapid generation of libraries of small heterocycles for biological screening. The reagent is commercially available, cheap, and highly chemoselective. The yields were superior in aqueous micelles to those in organic solvents. Short reaction times, large-scale synthesis, excellent chemoselectivity, excellent yields, as well as environmental friendliness are the main advantages of this diversity-oriented synthesis.
引用
收藏
页码:331 / 341
页数:11
相关论文
共 5 条
  • [1] Diversity-oriented synthesis of benzimidazole, benzoxazole, benzothiazole and quinazolin-4(3H)-one libraries via potassium persulfate–CuSO4-mediated oxidative coupling reactions of aldehydes in aqueous micelles
    Atul Kumar
    Ram Awatar Maurya
    Deepti Saxena
    Molecular Diversity, 2010, 14 : 331 - 341
  • [2] A FACILE SYNTHESIS OF DIVERSE LIBRARIES OF BENZIMIDAZOLE, BENZOXAZOLE, BENZOTHIAZOLE AND QUINAZOLIN-4(3H)-ONE VIA PPDS-CUSO4 MEDIATED REACTIONS OF ALDEHYDES IN AQUEOUS MICELLES
    Prasad, Siyaram
    Amber, Nausheen
    Kumar, Pratyoosh
    HETEROCYCLIC LETTERS, 2021, 11 (03): : 431 - 446
  • [3] One-pot synthesis of polysubstituted quinazolin-4(3H)-ones via sequential oxidative Ugi/Staudinger/aza-Wittig reactions starting from tertiary amines
    Sun, Mei
    Yu, Yan-Ling
    Zhao, Long
    Ding, Ming-Wu
    TETRAHEDRON, 2021, 96
  • [4] A green process PEG-600 mediated on-pot, alternative synthesis of 3-methyl-2-(((1-methyl-1H-benzimidazole-2-YL) sulfonyl) methyl) quinazolin-4(3H)-one
    Bireddy, Srinivasa Reddy
    Konkala, Veera Swamy
    Dubey, Pramod Kumar
    VIETNAM JOURNAL OF CHEMISTRY, 2020, 58 (06) : 798 - 803
  • [5] Palladium(II) N∧O Chelating Complexes Catalyzed One-Pot Approach for Synthesis of Quinazolin-4(3H)-ones via Acceptorless Dehydrogenative Coupling of Benzyl Alcohols and 2-Aminobenzamide
    Balaji, Sundarraman
    Balamurugan, Gunasekaran
    Ramesh, Rengan
    Semeril, David
    ORGANOMETALLICS, 2021, 40 (06) : 725 - 734