Literature DB >> 25758538

Highly efficient water-mediated approach to access benzazoles: metal catalyst and base-free synthesis of 2-substituted benzimidazoles, benzoxazoles, and benzothiazoles.

Manju Bala1, Praveen Kumar Verma, Deepika Sharma, Neeraj Kumar, Bikram Singh.   

Abstract

An efficient water-catalyzed method has been developed for the synthesis of 2-substituted benzimidazoles, benzoxazoles, and benzothiazoles in one step. The present method excludes the usage of toxic metal catalysts and bases to produce benzazoles in good to excellent yields. An efficient and versatile water-mediated method has been established for the synthesis of various 2-arylbenzazoles. The present protocol excludes the usage of any catalyst and additive provided excellent selectivities and yields with high functional group tolerance for the synthesis of 2-arylated benzimidazoles, benzoxazoles, and benzothiazoles. Benzazolones were also synthesized using similar reaction protocol.

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Year:  2015        PMID: 25758538     DOI: 10.1007/s11030-015-9572-8

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  40 in total

1.  Multicomponent reactions are accelerated in water.

Authors:  Michael C Pirrung; Koushik Das Sarma
Journal:  J Am Chem Soc       Date:  2004-01-21       Impact factor: 15.419

2.  Highly efficient synthesis and solid-state characterization of 1,2,4,5-tetrakis(alkyl- and arylamino)benzenes and cyclization to their respective benzobis(imidazolium) salts.

Authors:  Dimitri M Khramov; Andrew J Boydston; Christopher W Bielawski
Journal:  Org Lett       Date:  2006-04-27       Impact factor: 6.005

3.  2-Arylbenzoxazoles as CETP inhibitors: raising HDL-C in cynoCETP transgenic mice.

Authors:  Florida Kallashi; Dooseop Kim; Jennifer Kowalchick; You Jung Park; Julianne A Hunt; Amjad Ali; Cameron J Smith; Milton L Hammond; James V Pivnichny; Xinchun Tong; Suoyu S Xu; Matt S Anderson; Ying Chen; Suzanne S Eveland; Qiu Guo; Sheryl A Hyland; Denise P Milot; Anne-Marie Cumiskey; Melanie Latham; Laurence B Peterson; Raymond Rosa; Carl P Sparrow; Samuel D Wright; Peter J Sinclair
Journal:  Bioorg Med Chem Lett       Date:  2010-10-20       Impact factor: 2.823

Review 4.  Dehydrogenation as a substrate-activating strategy in homogeneous transition-metal catalysis.

Authors:  Graham E Dobereiner; Robert H Crabtree
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

5.  Hydrogen autotransfer in the N-alkylation of amines and related compounds using alcohols and amines as electrophiles.

Authors:  Gabriela Guillena; Diego J Ramón; Miguel Yus
Journal:  Chem Rev       Date:  2010-03-10       Impact factor: 60.622

6.  Oxidative kinetic self-sorting of a dynamic imine library.

Authors:  Karolina Osowska; Ognjen Š Miljanić
Journal:  J Am Chem Soc       Date:  2010-12-20       Impact factor: 15.419

7.  Rate acceleration of the Baylis-Hillman reaction in polar solvents (water and formamide). Dominant role of hydrogen bonding, not hydrophobic effects, is implicated.

Authors:  Varinder K Aggarwal; David K Dean; Andrea Mereu; Richard Williams
Journal:  J Org Chem       Date:  2002-01-25       Impact factor: 4.354

8.  Synthesis and antiviral evaluation of polyhalogenated imidazole nucleosides: dimensional analogues of 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole.

Authors:  Tun-Cheng Chien; Sunita S Saluja; John C Drach; Leroy B Townsend
Journal:  J Med Chem       Date:  2004-11-04       Impact factor: 7.446

9.  Synthesis and angiotensin II receptor antagonistic activities of benzimidazole derivatives bearing acidic heterocycles as novel tetrazole bioisosteres.

Authors:  Y Kohara; K Kubo; E Imamiya; T Wada; Y Inada; T Naka
Journal:  J Med Chem       Date:  1996-12-20       Impact factor: 7.446

10.  Antitumor benzothiazoles. 8. Synthesis, metabolic formation, and biological properties of the C- and N-oxidation products of antitumor 2-(4-aminophenyl)benzothiazoles.

Authors:  E Kashiyama; I Hutchinson; M S Chua; S F Stinson; L R Phillips; G Kaur; E A Sausville; T D Bradshaw; A D Westwell; M F Stevens
Journal:  J Med Chem       Date:  1999-10-07       Impact factor: 7.446

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