Recent Advancement in the Conversion of 1,2,3‐Benzotriazin‐4(3H)‐One to Other Heterocyclic Systems and Their Applications: A Concise Review

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(5)

Published: Feb. 1, 2025

Abstract The nitrogen containing 1,2,3‐benzotriazin‐4(3 H )‐one is structurally worthwhile system for its notable applications in the synthesis of N─ , O ─ and S─ heterocycles bears pivotal significant usage pharmaceutical industrial chemicals. Today most common items like dyes, cosmetics, sanitizers, insecticides plastics are based on heterocyclic moieties. Different starting materials used industrially formation diverse but a valuable structure to prepare numerous products. These conversions radiation or metal‐catalyzed denitrogenation annulation type reactions provide easy, one‐step atom‐economical route. vast significance their cheap make this subject interesting scientific researchers industrialists. This mini review summarizes recent developments transformation ring various other structures phenanthridinones, isoquinolones, coumarin‐1‐imines, benzamides, pyrroloquinazolinones, indolin‐1‐ones, 1,2‐benzisoselenazol‐3(2 )‐ones benzofuranones. Some emerging drugs ebselen, losartan, irbesartan, luotonin A, deoxyvasicinone mackinazolinone have been successfully synthesized from differently substituted benzotriazinones.

Language: Английский

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Mechanoredox/Nickel Co-Catalyzed Cross Electrophile Coupling of Benzotriazinones with Alkyl (Pseudo)halides

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(18), P. 12891 - 12901

Published: Aug. 24, 2023

An air-tolerant mechanoredox/nickel cocatalyzed cross electrophile coupling of benzotriazinones with alkyl (pseudo)halides is developed by liquid-assisting grinding in the presence manganese powders and strontium titanate as a reductant cocatalyst, respectively. Mechanical activation metal surfaces via ball milling eliminates chemical activator for manganese, while mechanoredox cocatalysis remarkably improves aryl/alkyl piezoelectricity-mediated radical generation from halides. Both display reactivities different those conventional thermal chemistry solution. The scope reaction demonstrated 26 examples, showing high chemoselectivity bromides vs chlorides.

Language: Английский

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Continuous Flow Synthesis of Benzotriazin-4(3H)-ones via Visible Light Mediated Nitrogen-Centered Norrish Reaction

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2371 - 2375

Published: March 11, 2024

We report a new protocol for the synthesis of substituted benzotriazin-4(3H)-ones which are underrepresented heterocyclic scaffolds with important pharmacological properties. Our method exploits acyclic aryl triazine precursors that undergo photocyclization reaction upon exposure to violet light (420 nm). Continuous flow reactor technology is exploited afford excellent yields in only 10 min residence time no additives or photocatalysts needed. The underlying mechanism appears be based on an unprecedented variation classical Norrish type II concomitant fragmentation and formation N–N bonds. Scalability, process robustness, green credentials this intriguing transformation highlighted.

Language: Английский

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Improved Palladium Catalysis in Suzuki‐Type Coupling of Benzotriazinones for o‐Aryl/Alkenyl Benzamides

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(11), P. 2623 - 2628

Published: April 20, 2024

Abstract A palladium catalyst system based on PdCl 2 (PPh 3 ) or (dppf) is reported for Suzuki‐type coupling of both N ‐aryl and alkyl benzotriazinones with aryl/alkenyl boronic acids to afford a series ortho ‐aryl/alkenyl benzamides in yields up 99%, showing improvements catalytic efficiency, substrate scope practicality. Scope limitations the improved protocol have been demonstrated more than 40 examples, including multigram‐scale synthesis activated o ‐biphenyl amide. Large electronic steric effects from acid counterpart observed, implying transmetallation boron should be involved rate‐determining step cycle.

Language: Английский

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Na₂S·9H₂O Enabled Defluorodisulfuration and Hydrodefluorination of Perfluorobutyl Tetralones: Synthesis of Trifluoromethyl 1,2-Dithioles

Organic Letters, Journal Year: 2023, Volume and Issue: 25(23), P. 4388 - 4393

Published: June 2, 2023

An unprecedented defluorocyclization of perfluorobutyl tetralones with Na2S·9H2O was developed for the synthesis trifluoromethyl 1,2-dithioles, which provided chemists novel access to biologically and pharmaceutically relevant organofluorides. Successive C(sp3)–F bond functionalization at perfluoroalkyl chain is vital formation four C–H/C–S/S–S bonds a five-membered S-heterocycle assembly. Cheap, weakly toxic, odorless inorganic sulfide acts as both disulfurating precursor hydrodefluorinating reagent in this tandem multi-bond-interconverting reaction.

Language: Английский

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Synthesis of ortho-Methylated Benzamides via Palladium-Catalyzed Denitrogenative Cross-Coupling Reaction of [1,2,3]-Benzotriazin-4(3H)-ones with DABAL-Me₃

Organic Letters, Journal Year: 2023, Volume and Issue: 25(29), P. 5443 - 5447

Published: July 13, 2023

We herein developed a palladium-catalyzed reaction of [1,2,3]-benzotriazin-4(3H)-ones with DABAL-Me3 [bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]octane adduct], cheap, stable, and solid organoaluminum reagent. In the presence Pd(OAc)2/XantPhos as commercially available catalyst, underwent denitrogenative coupling to afford wide array N-aryl amides derived from ortho-methylated carboxylic acids. Under same catalytic conditions, ortho-ethylation could also be achieved by using triethylaluminum.

Language: Английский

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Metal-free three-component tandem cyclization for modular synthesis of 2,3-dihydrobenzothiazin-4-ones

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 2021 - 2026

Published: Jan. 1, 2024

The first three-component cyclization reaction of benzo[ c ][1,2]dithiol-3-ones based on S–S bond cleavage is disclosed herein.

Language: Английский

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Recent advances in synthesis and transformations of 1,2,3-benzotriazinones

Journal of Organometallic Chemistry, Journal Year: 2024, Volume and Issue: 1013, P. 123156 - 123156

Published: April 25, 2024

Language: Английский

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Controllable Molecular Editing of 2-Amino-N-substituted Benzamides: Site-selective Synthesis of 6-Selenylated N-Substituted 1,2,3-Benzotriazine-4(3H)-ones

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 3, 2025

We present an efficient silver-catalyzed one-pot controllable molecular editing protocol for the transformation of 2-amino-N-substituted benzamides into 6-selenylated N-substituted 1,2,3-benzotriazine-4(3H)-ones under mild reaction conditions. This three-component strategy is achieved by building N-N/N═N/C-Se bonds, which provides a practical pathway preparation selenylated with broad substrate scope and good functional group tolerance, as well high site-selectivity. Mechanistic experiments suggest that this proceeds via intermolecular site-selective C-H selenylation readily available diselenides, followed annulation using AgNO3 nitrogen synthon.

Language: Английский

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TfOH-catalysed PPh3-Promoted Nucleophilic Cyclization Reactions for the Synthesis of Functionalized (Z)-2-imino-benzo[e][1,3]thiazin-4-ones

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134676 - 134676

Published: April 1, 2025

Language: Английский

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