Synthesis of aminobenzoxazoles via simple, clean and efficient electrochemical redox reactions

Ghoshal, Tanay; Nagar, Vishal; Vutla, Adilakshmi; Kotturi, Sharadsrikar; Kuttappan, Sasikumar

doi:10.1016/j.tetlet.2018.12.054

Cited by 8 publications

(3 citation statements)

References 19 publications

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“…In earlier work, we synthesized benzoxazoles, benthiazoles and benzimidazoles by using aluminum and carbon as the electrode system, acetic acid as an electrolyte and acetonitrile/methanol as the solvent. [16][17][18] Performing research on similar lines we electrochemically reacted benzaldehyde (1a) and 2-aminobenzamide (2a) in acetonitrile and after 3 h obtained 41% conversion (as per LCMS analysis). Encouraged by this result we screened a number of solvents (as listed in Table-1).…”

Section: Resultsmentioning

confidence: 99%

Electrochemical synthesis of 4-quinazolinone derivatives mediated by acetic acid

Ghoshal¹

2023

Arkivoc

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The acid-catalyzed cyclization of 2-aminobenzamides into 4-quinazolines was achieved using a combination of carbon and aluminum electrodes under electrochemical conditions. Overall, the method offers large substrate scope with good functional group tolerance using acetic acid as an inexpensive electrolyte. Quinazolin-4(3H)one and 2-methylquinazolin-4(3H)-one derivatives were also prepared under similar electrochemical conditions. The transformations occurred at room temperature with moderate to good yields. A few of the quinazolin-4(3H)-one cores were successfully transformed into compounds similar to known anticancer drugs.

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Section: Resultsmentioning

confidence: 99%

Electrochemical synthesis of 4-quinazolinone derivatives mediated by acetic acid

Ghoshal¹

2023

Arkivoc

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“…In our previous work [19] we had synthesised of 2‐amino benzoxazole using aluminium and carbon as the electrode system, TBAI as the electrolyte and acetonitrile as the solvent with 5 equivalent of acetic acid. On similar lines we electrochemically reacted 1,2 diamino benzene ( 1 a ) and 4‐chloro benzaldehyde ( 2 a ) and we obtained 30 % conversion in LCMS after 3 hours.…”

Section: Resultsmentioning

confidence: 99%

Acetic Acid Mediated Electrochemical Synthesis of Benzazole and its Application in the Synthesis of Pharmaceutically Active Compounds

2021

Self Cite

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An acetic acid promoted electrochemical synthesis of benzazoles, benzimidazoles, benzthiazoles and benzoxazoles, is reported. The method offers large substrate scope, good functional group tolerance, while using cheap electrolyte. The method uses acetic acid as the electrolyte which has a better solubility in methanol, hence the reaction time is less and product formation is observed in high yield without much side product. This electrochemical method is further utilised to synthesise thiabendazole, fuberidazole, chlormidazole and advance intermediates of bilastine and clemizole in good yields.

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“…2-Aminobenzoxazole was successfully synthesised from benzoxazole and N-heterocycles by using different electrodes and electrolytes. [51] Maximum conversion was accomplished when aluminium and carbon were utilized as the cathode and anode respectively, in tetrabutylammonium iodide (TBAI) as the electrolyte. Multiple trials were conducted at room temperature, and N-Boc piperazine provided excellent yield among various N-heterocycles.…”

Section: Non-metal-catalyzed Aminationmentioning

confidence: 99%

Recent Advances and Prospects in the Amination of Benzoxazoles

Ibrahim¹,

Saranya²,

Anilkumar³

2022

ChemistrySelect

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Aminoheterocycles are important class of heterocycles and many of the natural products and drug molecules are observed as the derivatives of aminoheterocycles. Consequently, their efficient synthetic protocols have gained more attention among organic chemists. Benzoxazole is one of the familiar fused heterocyclic compounds showing vibrant biological activities, and is seen as the backbone in various biologically important compounds and drugs. The new C−N bond construction on benzoxazole by the coupling between sp2 carbon at the 2‐position of benzoxazole and nitrogen from several nitrogen sources enhanced their properties, and the area of amination of benzoxazole is relatively rich in literature. In this review, we have compiled the recent advances in the amination of benzoxazoles by giving an overview and covering literature up to 2021.

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Synthesis of aminobenzoxazoles via simple, clean and efficient electrochemical redox reactions

Cited by 8 publications

References 19 publications

Electrochemical synthesis of 4-quinazolinone derivatives mediated by acetic acid

Electrochemical synthesis of 4-quinazolinone derivatives mediated by acetic acid

Acetic Acid Mediated Electrochemical Synthesis of Benzazole and its Application in the Synthesis of Pharmaceutically Active Compounds

Recent Advances and Prospects in the Amination of Benzoxazoles

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