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

ChemistrySelect, Год журнала: 2025, Номер 10(5)

Опубликована: Фев. 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.

Язык: Английский

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

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(18), С. 12891 - 12901

Опубликована: Авг. 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.

Язык: Английский

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

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(11), С. 2623 - 2628

Опубликована: Апрель 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.

Язык: 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, Год журнала: 2023, Номер 25(29), С. 5443 - 5447

Опубликована: Июль 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.

Язык: Английский

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

Journal of Organometallic Chemistry, Год журнала: 2024, Номер 1013, С. 123156 - 123156

Опубликована: Апрель 25, 2024

Язык: Английский

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Visible light-induced denitrogenative annulation reaction of 1,2,3-benzotriazin-4(3H)-ones with alkenes and alkynes via electron donor–acceptor (EDA) complex formation: a sustainable approach to isoindolinone and isoquinolinone synthesis

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(21), С. 6184 - 6193

Опубликована: Янв. 1, 2024

An efficient metal-free approach for the synthesis of isoindolinones and isoquinolinones from 1,2,3-benzotriazin-4(3 H )-ones via electron donor–acceptor (EDA) complex formation under visible light is described.

Язык: Английский

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Magnesium-Mediated Cross-Electrophile Couplings of Aryl 2-Pyridyl Esters with Aryl Bromides for Ketone Synthesis through In Situ-Formed Arylmagnesium Intermediates

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(18), С. 13661 - 13668

Опубликована: Сен. 9, 2024

Aryl 2-pyridyl esters could efficiently undergo cross-electrophile couplings with aryl bromides the aid of magnesium as a reducing metal in absence transition-metal catalyst, leading to unsymmetrical diaryl ketones modest good yields wide functionality compatibility. In addition, reaction be easily scaled up and applied late-stage modification biologically active molecules. Preliminary mechanistic study showed that coupling presumably proceeds through situ formation arylmagnesium reagents key intermediates.

Язык: Английский

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Electrochemical Cascade Reactions of 1,2,3-Benzotriazinones with Alkynes to Assemble 3,4-Dihydroisoquinolin-1(2H)-ones

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 21, 2025

An unexpected electrochemical cascade reaction of 1,2,3-benzotriazinones with alkynes to assemble 3,4-dihydroisoquinolin-1(2H)-ones has been developed, which avoids the use pressurized H2, any metal catalysts, and stoichiometric redox agents. This route tolerates a wide range functional groups in both reactants can be performed under an air atmosphere. The process continuous cathodic reduction was demonstrated by control experiments cyclic voltammograms. Moreover, gram-scale confirmed potential this environmentally benign method for practical applications.

Язык: Английский

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Denitrogenative transformations of aryl-fused 1,2,3-triazoles

Advances in heterocyclic chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

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Iodide/Nickel Co-Catalyzed Manganese-Mediated Denitrogenative Cross-Electrophile Coupling of Benzotriazinones with Alkyl Sulfonates

Molecules, Год журнала: 2025, Номер 30(11), С. 2397 - 2397

Опубликована: Май 30, 2025

An efficient Ni-catalyzed, Mn-mediated denitrogenative cross-electrophile coupling of N-alkyl-1,2,3-benzotriazinones with alkyl tosylates and mesylates for access to o-alkyl secondary benzamides is reported. The method uses inexpensive non-anhydrous dimethyl acetamide (DMA) in combination tetrabutyl ammonium iodide (TBAI) as a co-catalyst convert sulfonates into iodides situ. Scope limitations the protocol have been demonstrated by >30 examples yields up 91%, showing large electronic effect from N-substituent benzotriazinones. unexpected steric acceleration has observed core benzotriazinones, not only promising highly 2-alkyl-2,3-disubstituted but also shedding light on rate-limiting steps catalytic cycle.

Язык: Английский

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