Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

Chemical Reviews, Год журнала: 2024, Номер unknown

Опубликована: Сен. 13, 2024

Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. iodine are commonly used synthetically important halogenations, oxidations, aminations, heterocyclizations, various oxidative functionalizations of substrates. Iodonium salts arylating reagents, while iodonium ylides imides excellent carbene nitrene precursors. Various derivatives benziodoxoles, such azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, alkenylbenziodoxoles group transfer the presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Development hypervalent catalytic systems discovery highly enantioselective reactions chiral represent a particularly recent achievement field chemistry. Chemical transformations promoted by many cases unique cannot be performed any other common, non-iodine-based reagent. This review covers literature published mainly last 7-8 years, between 2016 2024.

Язык: Английский

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Review of synthesis process of benzoxazole and benzothiazole derivatives

Synthetic Communications, Год журнала: 2024, Номер 54(10), С. 769 - 801

Опубликована: Апрель 5, 2024

Benzoxazoles and benzothiazoles are a class of aromatic heterocyclic compounds having similar ring structures, in which benzene is fused to the 4 5 positions 1,3-oxazole 1,3-thiazole rings respectively. They constitute an interesting organic due their powerful significant biological, agrochemical, pharmaceutical physicochemical activities. Indeed, benzoxazole benzothiazole derivatives possess wide range applications, such as: anticancer, anti-inflammatory, antioxidant, anticonvulsant, antitubercular, antifungal, pesticidal, anticorrosive, complexing properties so on. The synthesis has attracted much attention from several researchers across world numerous synthetic methods have been developed access these over past decades. In this review, we present new recent strategies, as well some biological derivatives.

Язык: Английский

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Electrochemically Promoted Three-Component Reaction to N-Sulfonyl Amidines

Organic Letters, Год журнала: 2023, Номер 26(1), С. 193 - 197

Опубликована: Дек. 26, 2023

In this study, a multicomponent reaction via the Mannich intermediate was developed using methanol, secondary amine, and sulfonamide as starting materials. This method uses methanol green C1 source. The substrate scope is wide, yield good. mechanistic study shows that generates formaldehyde under electrochemical conditions, sulfonyl amidine nucleophile reacts with Schiff base intermediates to form N-sulfonyl in single step.

Язык: Английский

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Hypervalent Iodine Promoted Selective [2 + 2 + 1] Cycloaddition of Aromatic Ketones and Methylamines: A One-Pot Access to 1-Pyrrolines

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 9958 - 9971

Опубликована: Июль 9, 2024

Herein, a versatile highly regioselective three-component annulation of simple aromatic ketones and methylamines using hypervalent iodine reagent for polyarylated 1-pyrrolines has been described in good to excellent yields. Meanwhile, unsymmetrical 1-pyrroline isomers could be realized synthesized. Such an intriguing one-pot two-step tandem assembly strategy with green conditions high regioselectivity shows predictable inspiration related reactions.

Язык: Английский

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Hypervalent Iodine Mediated Synthesis of 2‐Aminobenzazoles and 2‐Aminobenzothiazoles

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(6)

Опубликована: Апрель 6, 2024

Abstract The hypervalent iodine mediated, silica gel promoted synthesis of 2‐aminobenzazoles and 2‐aminobenzothiazole derivatives under metal‐free mild conditions within short time (30 min) has been developed. Under this process, PhI(COOCF 3 ) 2 (PIFA) or PhI(COOCH (PIDA) acts as an oxidant radical initiator direct activated the ortho ‐C−H bond substrate, weakly lewis acid effectively increased reactivity reaction system. This method is compatible with various arylurea arylthiourea substrates, which green, efficient, simple to operate suitable for practical application.

Язык: Английский

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TBAB-catalyzed assisted C-C/C-N bond formations: An efficient approach to dihydrobenzo[ b ][1,8]naphthyridin derivatives via metal free Cascade annulation

Synthetic Communications, Год журнала: 2024, Номер 54(15), С. 1252 - 1262

Опубликована: Июль 22, 2024

Язык: Английский

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Synthesis of functionalized tetrahydrodibenzo[b,g][1,8]naphthyridin-1(2H)-ones through base-promoted annulation of quinoline-derived dipolarophiles and cyclic enaminones

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(48), С. 9524 - 9529

Опубликована: Янв. 1, 2023

An eco-friendly and metal-free method for the synthesis of tetrahydrodibenzo[b,g][1,8]naphthyridin-1(2H)-ones was established. Quinoline-derived dipolarophiles cyclic enaminones as starting materials undergo a 1,4-Michael addition/SNAr tandem annulation reaction affording target products. This approach features transition conditions, good functional group tolerance operational simplicity.

Язык: Английский

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Iron‐Promoted Redox Access to 2‐Aminobenzoxazoles from Amines, Carbon Disulfide and 2‐Nitrophenols

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Авг. 14, 2024

Abstract A method to assemble 2‐aminobenzoxazoles via iron‐catalyzed redox condensation of amines, carbon disulfide and 2‐nitrophenols is reported. The reaction features advantages environmentally friendly iron catalyzed conditions, readily available starting materials, excellent atom‐, step‐ redox‐ economy compared known protocols. Experimental investigation suggests a mechanism encompassing reduction the nitro group by dithiocarbamate from amine‐CS 2 adduct.

Язык: Английский

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Ultrasound-promoted synthesis of polysubstituted imidazole-linked benzoxazole derivatives and the investigation of their optical properties

Journal of Molecular Structure, Год журнала: 2024, Номер unknown, С. 140071 - 140071

Опубликована: Сен. 1, 2024

Язык: Английский

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