Eco-Friendly Syntheses of 2-Substituted Benzoxazoles and 2-Substituted Benzothiazoles from 2-Aminophenols, 2-Aminothiophenols and DMF Derivatives in the Presence of Imidazolium Chloride

Tian, Qingqiang; Luo, Wen; Zhang, Gan; Li, Dan; Dai, Zeshu; Wang, Huajun; Wang, Xuetong; Yuan, Jianyong

doi:10.3390/molecules24010174

Cited by 24 publications

(5 citation statements)

References 49 publications

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“…Tian and coworkers [119] unveiled an easy route to prepare 2-substituted BT employing 2-ABTs and DMFs at significant yields (60-87%). The reaction was performed in the presence of imidazolium chloride at 140 • C within 8-10 h. Some of the primary challenges of the reaction are the prolonged time, column chromatography use, and elevated temperatures (Scheme 41).…”

Section: Reaction Of 2-abt and Dimethylformamide (Dmf)derivativesmentioning

confidence: 99%

Pioneering Synthetic Strategies of 2-Substituted Benzothiazoles Using 2-Aminothiophenol

Teli,

Sethiya,

Agarwal

2024

Chemistry

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Heterocycles, compounds featuring heteroatoms like nitrogen, sulfur, and oxygen, are integral in fields such as synthesis, pharmacology, and medicine. Among these, benzothiazoles, formed by fusing thiazole with benzene, hold significant prominence. Their unique reactivity, especially at the carbon position between nitrogen and sulfur, has sparked wide interest. Notably, 2-substituted benzothiazoles exhibit diverse biological activities, including anticonvulsant, antimicrobial, and antioxidant properties, making them valuable in drug discovery. This review unveils an array of mesmerizing methods employed by chemists to prepare these compounds using 2-aminothiophenol as one of the precursors with other varied reactants. From novel strategies to sophisticated methodologies, each section of this review provides a glimpse into the fascinating world of synthetic chemistry of 2-substituted benzothiazoles. Delving into the diverse synthetic applications of 2-substituted benzothiazoles, this paper not only enriches our understanding of their synthesis but also sparks the imagination with the possibilities for future advancements.

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Section: Reaction Of 2-abt and Dimethylformamide (Dmf)derivativesmentioning

confidence: 99%

Pioneering Synthetic Strategies of 2-Substituted Benzothiazoles Using 2-Aminothiophenol

Teli,

Sethiya,

Agarwal

2024

Chemistry

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“…A simple, economical, and metal-free approach for the synthesis of 2-substitutedBTs 90 was reported in 60-87% yields from the condensation of substituted ATP and DMF derivatives, using imidazolium chloride (50% mmol) as the only promoter, without any other additive (Scheme 70) [178]. The proposed mechanistic pathway is as described in Scheme 71.…”

Section: Condensation With Amidesmentioning

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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“…The resulting mixture was poured into 40% sodium bicarbonate solution with stirring till precipitate has formed. The solid was filtered, washed with water and recrystallized from ethanol [32][33][34][35] .…”

Section: Chemistrymentioning

confidence: 99%

Untitled

2021

IJPSR

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Benzoxazole and its analogues play an important role as therapeutic agents and exhibit good cytotoxic as well as antimicrobial activity. In the present study, benzoxazole analogues have been prepared by synthetic route; their spectroscopic evaluation was carried out, and then the synthesized compounds were screened for their cytotoxic activity by Allium cepa root model as well as antimicrobial activity by cup plate method. The synthesis and cytotoxic activity of a novel series of Schiff's base was carried out by reacting the amino group of the 4-Benzoxazol-2yl-phenylamine with different aromatic/ heteroaromatic aldehydes in the presence of polyphosphoric acid to give 4-(1,3-Benzoxazol-2-yl)phenyl]-1-(Substituted phenyl) methanimine (4a-4h) also Diazotization reaction of (4-Benzoxazol-2-yl phenyl) with β napthol gave 2- ((4-(benzo [d]oxazole-2-yl)phenyl) diazenyl) naphthalene-2-ol (4i). The cytotoxic and antimicrobial activities of the synthesized compounds were determined by using the onion root model and cup plate method, respectively. The activity data of compounds was compared with standard drugs Cefixime for antibacterial activity and miconazole for antifungal was used as a standard, and cyclophosphamide was used as a standard for Cytotoxic activity.

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Eco-Friendly Syntheses of 2-Substituted Benzoxazoles and 2-Substituted Benzothiazoles from 2-Aminophenols, 2-Aminothiophenols and DMF Derivatives in the Presence of Imidazolium Chloride

Cited by 24 publications

References 49 publications

Pioneering Synthetic Strategies of 2-Substituted Benzothiazoles Using 2-Aminothiophenol

Pioneering Synthetic Strategies of 2-Substituted Benzothiazoles Using 2-Aminothiophenol

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

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