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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Rhodium-Catalyzed Atroposelective C–H Alkylation of 1-Aryl Isoquinoline Derivatives with Cyclopropanols

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 4017 - 4024

Published: Feb. 20, 2025

Language: Английский

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Metal-Catalyzed Transformations of Cyclopropanols via Homoenolates

Bulletin of the Chemical Society of Japan, Journal Year: 2020, Volume and Issue: 94(1), P. 265 - 280

Published: Sept. 28, 2020

Abstract Metal homoenolates represent uniquely useful organometallic intermediates in synthetic chemistry, allowing umpolung synthesis of β-functionalized carbonyl compounds. While siloxycyclopropanes had been established as reliable precursors to homoenolates, often stoichiometric, for diverse carbon–carbon bond forming reactions, unprotected cyclopropanols have emerged alternative and attractive catalytically generated, carbon–heteroatom bond-forming reactions. This review article provides an overview the development such homoenolate transformations, classified with respect metals involved cyclopropane ring opening.

Language: Английский

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A comprehensive survey upon diverse and prolific applications of chitosan-based catalytic systems in one-pot multi-component synthesis of heterocyclic rings

International Journal of Biological Macromolecules, Journal Year: 2021, Volume and Issue: 186, P. 1003 - 1166

Published: June 24, 2021

Language: Английский

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Nickel-Catalyzed Carbonylation of Cyclopropanol with Benzyl Bromide for Multisubstituted Cyclopentenone Synthesis

Organic Letters, Journal Year: 2022, Volume and Issue: 24(14), P. 2699 - 2704

Published: April 7, 2022

Herein, we reported a Ni-catalyzed carbonylation of cyclopropanol with benzyl bromide to afford multisubstituted cyclopentenone under 1 atm CO. The reaction proceeds through cascade bromides, followed by generation nickel homoenolate from cyclopropanols via β-C elimination 1,4-diketones, which undergoes intramolecular Aldol condensation furnish highly substituted derivatives in moderate good yields. exhibits high functional group tolerance broad substrate scope.

Language: Английский

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Metal-catalyzed reactions of organic nitriles and boronic acids to access diverse functionality

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(21), P. 4243 - 4277

Published: Jan. 1, 2022

This review summarises the latest reactions of boronic acids with functionalized nitriles in presence transition-metal catalysts.

Language: Английский

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Electrochemical Synthesis of β-Functionalized Ketones via Ring-Opening of Cycloalkanols

Organic Letters, Journal Year: 2022, Volume and Issue: 24(24), P. 4421 - 4426

Published: June 10, 2022

The electrochemical deconstructive functionalization of cycloalkanols with nucleophiles has been studied, which allows to occur exclusively at the β-position ketones. substrate scope includes a wide range as well diverse N, O, C, and P-centered nucleophiles, providing ready access β-functionalized ketones products. Mechanistic studies support generation α,β-unsaturated key intermediates followed by Michael addition nucleophiles.

Language: Английский

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Combination of Tetrazole and 4-Azido-pyrazolotriazine Oxide: Balance of High Nitrogen, Energy, and Safety

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

Published: Jan. 14, 2025

Energetic materials containing a pyrazolotriazine oxide skeleton have the potential for high performance. However, research on is very limited due to inherent ring system instability and synthetic approaches. In this paper, APTO OPTO with combination of high-nitrogen tetrazole promising azido-pyrazolotriazine been synthesized. Of these, its energetic salts exhibit excellent detonation properties (Dv > 8220 m s–1; P 26.50 GPa). Surprisingly, exhibits performance = 8913 32.43 GPa) comparable that RDX.

Language: Английский

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Palladium-catalyzed selective C–C bond cleavage and stereoselective alkenylation between cyclopropanol and 1,3-diyne: one-step synthesis of diverse conjugated enynes

Chemical Science, Journal Year: 2022, Volume and Issue: 13(9), P. 2692 - 2700

Published: Jan. 1, 2022

Palladium-catalyzed tandem activation and functionalization of readily accessible cyclopropanols have been demonstrated to access valuable conjugated enynes from 1,3-diynes with high stereo-selectivity.

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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