Metal-free C–H mercaptalization of benzothiazoles and benzoxazoles using 1,3-propanedithiol as thiol source

Yan, Xiao; Jing, Bing; Liu, Xiaoxia; Xue, Hongyu; Liu, Yajun

doi:10.3762/bjoc.15.24

Cited by 9 publications

(2 citation statements)

References 38 publications

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“…1) constitute a very interesting compound family due to their applications not only in organic synthesis, but also in the biomedical field as antibacterial, antiviral, anti-inflammatory, analgesic and anthelmintic agents. [13][14][15][16][17] Moreover, interesting studies have shown that the complexes of 2-mercaptobenzoxazoles with various transition metals possess a cytotoxic activity against cancer cells. 18…”

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confidence: 99%

2-Mercaptobenzoxazoles: a class of carbonic anhydrase inhibitors with a novel binding mode to the enzyme active site

et al. 2020

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2-Mercaptobenzoxazoles: a class of carbonic anhydrase inhibitors with a novel binding mode to the enzyme active site

et al. 2020

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“…Benzoxazole ring containing antibiotic, calcymicin reported by Evans 4 . Benzoxazole moieties are also reported to exhibit various biological activities like antihistaminic activity 5 , antimicrobial activity, analgesic 6 , antiinflammatory activity 7 , anti-mycobacterial 8 , anticancer 9 , anthelmintic activity 10 , hypoglycaemic activity 11 , antiviral 12 , herbicidal 13 , diuretic and uricosuric activities 14 .…”

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2020

IJPSR

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In view of the biological prominence of the benzoxazole derivatives as well as, isatin derivatives, it was planned to synthesize some novel N-(Benzoxazol-2-yl)-2-(2-oxoindolin-3ylidine) hydrazine carbothioamides (VI) as such reports were not available in the literature and were screened for antibacterial, antifungal and anti-mycobacterial activity. Fourteen new compounds were synthesized by condensing different Isatins (V) with N-(Benzoxazol-2-yl) hydrazine carbothioamide (IV). All the prepared compounds were screened for antibacterial, antifungal, and antimycobacterial activities on various microbial strains. The results revealed that all the synthesized compounds were exhibiting antimicrobial properties. Compound VIc, VIe, VIg, VIi, and VIl were declared to possess potent antimicrobial properties in the given bacterial and fungal strains. INTRODUCTION:Benzoxazole (m.p 27-30 °C; b.p. 182 °C), is a planar molecule with conjugated π electrons sextets in the cyclic system. The chemical properties are aromatic in character 1 . The lone pair of electrons on nitrogen, which is coplanar with the heterocyclic ring and, therefore, not involved in delocalization, confers weakly basic properties. Associated with the aromatic is a degree of stability, but when these are quarternized, the resulting azolium species are significantly activated towards nucleophilic attack 2 . Benzoxazole (pharmacophore) derivatives are biologically active compounds and are known to exhibit various biological activities such as anticancer, antimicrobial, anti-HIV, etc.

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A Review on Functionalization of Benzo‐5,6‐Fused Bicyclic Heteroaromatic Compounds

Pradeep Kumar,

Annie,

Kumar Bind

et al. 2024

Chemistry An Asian Journal

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Over the decades, functionalized heteroaromatic compounds and their scaffolds have drawn the significant attention in synthetic organic chemistry as well as in interdisciplinary sciences due to their prevalence in natural products, hormones, vitamins, and their applications in pharmaceuticals, agrochemicals, veterinary products, dyes and pigments, bio‐imaging, semiconductors, and optoelectronics, etc. This review explores various synthetic strategies for functionalization of numerous 5,6 benzo‐fused heteroaromatic derivatives such as indole, aza‐indole, benzofuran, benzothiophene, benzimidazole, benzoxazole, benzothiazole and benzotriazole through various methods including C‐H activation, cross‐coupling, metal catalysis, photo‐catalysis, electrocatalysis and organocatalysis in recent years (2019‐2023). Highly functionalized heterocyclic scaffolds are the important precursors for synthesizing many bioactive drugs like fenbendazole, viozan, Griseofulvin, zileuton, flunoxaprofen, natural products, and optoelectronic materials, etc.

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Metal-free C–H mercaptalization of benzothiazoles and benzoxazoles using 1,3-propanedithiol as thiol source

Cited by 9 publications

References 38 publications

2-Mercaptobenzoxazoles: a class of carbonic anhydrase inhibitors with a novel binding mode to the enzyme active site

2-Mercaptobenzoxazoles: a class of carbonic anhydrase inhibitors with a novel binding mode to the enzyme active site

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A Review on Functionalization of Benzo‐5,6‐Fused Bicyclic Heteroaromatic Compounds

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