Samarium(III) triflate: a new catalyst for facile synthesis of benzothiazoles and benzoxazoles from carboxylic acids in aqueous media

Gorepatil, Pratapsinha B.; Mane, Yogesh D.; Gorepatil, Amarsinha; Gaikwad, Mahadev V.; Ingle, Vilas S.

doi:10.1007/s11164-014-1897-x

Cited by 12 publications

(6 citation statements)

References 48 publications

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“…Short reaction times, aqueous reaction media, and easy work-up are the advantages of this method. The catalysts were reused without any appreciable loss of efficiency [134].…”

Section: Other Acids As Catalystsmentioning

confidence: 99%

Benzothiazoles from Condensation of o-Aminothiophenoles with Carboxylic Acids and Their Derivatives: A Review

et al. 2021

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Nowadays, organic chemists are interested in the field of heterocyclic chemistry due to its use in the synthesis of a great variety of biologically active compounds. Heterocyclic compounds are widely found in nature and are essential for life. Among these, some natural nitrogen containing heterocyclic compounds have been used as chemotherapeutic agents. Their attachment to sugar molecules either as thioglycosides or as nucleosides analogues plays an important role in vital biological processes as well as in synthetic organic chemistry. Molecules containing benzothiazole (BT) nuclei are of this interesting class of compounds because some of them have been found to have a wide variety of biological activities. In this sense, we selected this topic to review and to then summarize the procedures related to the condensation reactions of o-aminothiophenoles (ATPs) as well as their disulfides with carboxylic acids, esters, orthoesters, acyl chlorides, amides, and nitriles. The condensation reactions with carbon dioxide (CO2) are included. Conventional methods with the use of acid and metal catalysts as well as recent green techniques, such as microwave irradiation, the use of ionic liquids, and ultrasound (US) chemistry, which have proven to have many advantages, were found in the review.

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“…Short reaction times, aqueous reaction media, and easy work-up are the advantages of this method. The catalysts were reused without any appreciable loss of efficiency [134].…”

Section: Other Acids As Catalystsmentioning

confidence: 99%

Benzothiazoles from Condensation of o-Aminothiophenoles with Carboxylic Acids and Their Derivatives: A Review

et al. 2021

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“…did an eco‐friendly synthesis of benzimidazoles ( 103 and 104 ) by refluxing o ‐phenylenediamines ( 102 ) with aldehydes and carboxylic acids catalyzed in the presence of a Lewis acid water soluble catalyst, zirconyl nitrate, ZrO (NO 3 ) 2 (5 mol %). The yield was 76–98% when 102 reacted with aldehydes in 2–4.5 h, while it was 78–96% for carboxylic acids in 2.5–4.5 h (Scheme ) .…”

Section: Oxidative Coupling Of O‐phenylenediamine Using Transition Mementioning

confidence: 99%

Recent Trends in the Synthesis of Benzimidazoles From o‐Phenylenediamine via Nanoparticles and Green Strategies Using Transition Metal Catalysts

Singhal

Khanna

Panda

et al. 2019

Journal of Heterocyclic Chem

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Benzimidazole is a heterocyclic moiety of immense importance as it acts as a primary “biolinker” in diverse synthetic routes to obtain bioactive compounds. Substituted benzimidazoles are known to possess a varied range of pharmacological applications, namely, anti‐cancer, anti‐diabetic, anti‐inflammatory, and antiviral like anti‐HIV and anti‐fungal. A number of reviews covering the important aspects of benzimidazoles such as pharmacological activities, SAR studies, and well‐known methods of synthesis have appeared in the literature. However, green synthetic methods particularly using transition metal (TM) catalysts and their nanoparticles, although being more viable and extensively applied by researchers in the present scenario, have not been exclusively and expansively reviewed. Besides this, the vital precursors required for knitting the skeleton of benzimidazole are mainly o‐aryldiamines. The conventional synthesis generally involved the condensation of these diamines with carbonyl/carboxylic acid derivatives either via high temperature heating or via adding strong acids, mostly resulting in poor yields or mixtures. However, recent trends are replacing these conditions by mild and green conditions through TM catalysts. Therefore, the current review emphasizes on the recent trends adopted in the synthesis of benzimidazoles using condensation reaction of o‐phenylenediamines and various aldehydes/ester/amide/alcohols with TM in a catalytic role in nanoform and under environmentally benign green conditions.

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“…Concisely, diverse functionalized substituted benzimidazole derivatives 30–38 have been synthesized in moderate to high yields by reaction of susbstituted‐ o ‐phenylenediamine with benzaldehyde and heteroaromatic aldehyde derivatives in the presence of heterogeneous catalysts such as Cu(II) containing nanosilica for the synthesis of 30 , ZrO(NO 3 ) 2 for 31 , nano CeO 2 for 32 , CuI for 33 , 3,6‐di(pyridin‐4‐yl)‐1,2,4,5‐tetrazine for 34 , NaHSO 3 /H 2 O 2 for 35 , SO 4 2− –ZrO 2 for 36 , Na 2 S 2 O 5 for 37 , and Na 2 S 2 O 4 for 38 (Table ).…”

Section: Chemistrymentioning

confidence: 99%

Functionalized Benzimidazole Scaffolds: Privileged Heterocycle for Drug Design in Therapeutic Medicine

Ajani

Aderohunmu

Ikpo

et al. 2016

Archiv der Pharmazie

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Benzimidazole derivatives are crucial structural scaffolds found in diverse libraries of biologically active compounds which are therapeutically useful agents in drug discovery and medicinal research. They are structural isosteres of naturally occurring nucleotides, which allows them to interact with the biopolymers of living systems. Hence, there is a need to couple the latest information with the earlier documentations to understand the current status of the benzimidazole nucleus in medicinal chemistry research. This present work unveils the benzimidazole core as a multifunctional nucleus that serves as a resourceful tool of information for synthetic modifications of old existing candidates in order to tackle drug resistance bottlenecks in therapeutic medicine. This manuscript deals with the recent advances in the synthesis of benzimidazole derivatives, the widespread biological activities as well as pharmacokinetic reports. These present them as a toolbox for fighting infectious diseases and also make them excellent candidates for future drug design.

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Samarium(III) triflate: a new catalyst for facile synthesis of benzothiazoles and benzoxazoles from carboxylic acids in aqueous media

Cited by 12 publications

References 48 publications

Benzothiazoles from Condensation of o-Aminothiophenoles with Carboxylic Acids and Their Derivatives: A Review

Benzothiazoles from Condensation of o-Aminothiophenoles with Carboxylic Acids and Their Derivatives: A Review

Recent Trends in the Synthesis of Benzimidazoles From o‐Phenylenediamine via Nanoparticles and Green Strategies Using Transition Metal Catalysts

Functionalized Benzimidazole Scaffolds: Privileged Heterocycle for Drug Design in Therapeutic Medicine

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