Cycloaddition Reactions of Enamines

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(14)

Published: Feb. 6, 2023

Abstract This review includes information for around two last decades on cycloaddition reactions of enamines with various agents in order to build carbo‐ and heterocycles. In addition, the presents organo‐catalytic which are intermediate products generated situ. covers synthesis four, five, six eight‐membered carbocyclic compounds, as well heterocycles pyrroles, pyridines, etc.

Language: Английский

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Catalytic Synthesis of Atropoisomers via Non‐Canonical Friedel‐Crafts Reactions

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(8), P. 1670 - 1706

Published: Feb. 29, 2024

Abstract The Friedel‐Crafts reaction stands as a powerful synthetic tool for C−H functionalization of aromatic feedstocks, which is conventionally realized through electrophilic alkylation and acylation. burgeoning interests in axially chiral compounds across diverse fields have spurred extensive exploration this classic transformation catalytic atroposelective synthesis. Consequently, the past decade has witnessed rapid expansion various non‐canonical reactions, including arylation, alkenylation, halogenation, sulfenylation, amination aryl bonds, thereby delving into new chemical spaces. A range methods been devised these significant arene functionalization. This review provides comprehensive overview cutting‐edge synthesis atropoisomers categorized three parts based on type bond formation aromatics: C( sp 2 )−C( 3 ) formations, formations )−heteroatom formations. richness electrophiles modulation atroposelectivity by organocatalysts, particularly Brønsted acids, are elucidated. We anticipate that repertoire asymmetric will continue to flourish be demonstrated not only scientific researches but also industrial organic

Language: Английский

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Synthesis of cyclopenta[b]benzofurans via biomimetic oxidative phenol–enamine [3 + 2] cycloaddition

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(5), P. 1213 - 1218

Published: Jan. 1, 2023

A hemin/ t -BuOOH-catalyzed oxidative phenol–enamine formal [3 + 2] cycloaddition has been developed, enabling the environmentally benign synthesis of valuable cyclopenta[ b ]benzofuran scaffolds under sustainable reaction conditions.

Language: Английский

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Hemin-Catalyzed Oxidative Phenol-Hydrazone [3+3] Cycloaddition Enables Rapid Construction of 1,3,4-Oxadiazines

Organic Letters, Journal Year: 2020, Volume and Issue: 22(17), P. 6911 - 6916

Published: Aug. 24, 2020

Herein, we present a hemin-catalyzed oxidative phenol-hydrazone [3+3] cycloaddition that accommodates broad spectrum of N-arylhydrazones, class less exploited 1,3-dipoles due to their significant Lewis basicity and weak tendency undergo 1,2-prototropy form azomethine imines. It renders expedient assembly diversely functionalized 1,3,4-oxadiazines with excellent atom step economy. Preliminary mechanistic studies point the involvement one-electron oxidation pathway, which likely differs from base-promoted aerobic scenario.

Language: Английский

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Bimetallic copper/cobalt-cocatalyzed double aerobic phenol oxidation/cyclization toward π-extended benzofuro[2,3-b]indoles as electron donors for electroluminescence

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(14), P. 5031 - 5036

Published: Jan. 1, 2021

π-Extended benzofuro[2,3-b]indoles were efficiently constructed from readily available p-hydroquinone esters and indoles via aerobic oxidation.

Language: Английский

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Synthesis of isochromanonesvialaccase-mediated oxidative [4 + 2] cyclization of pyrocatechuic acid with styrenes

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(14), P. 5598 - 5603

Published: Jan. 1, 2022

Isochromanone is the core structure of many active natural products.

Language: Английский

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Synthesis and X-ray characterization of two new 1,4-benzoxazine derivatives: Structural analysis and DFT calculations

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1315, P. 138802 - 138802

Published: June 1, 2024

The synthesis and XRD characterization of two new 1,4-benzoxazine derivatives (3a-5a) namely ethyl‐6‐nitro‐3a‐(p‐tolylamino)‐1,2,3,3a‐tetrahydrobenzo[b]cyclopenta[e][1,4]oxa-zine‐9a(9H)‐carboxylate (3a) methyl-6,10b-dimethyl-5a,6,10b,11-tetrahydrobenzo[5,6][1,4]oxazino[2,3-b]indole-2-carboxylate (5a) are reported herein. In both compounds it is observed the formation π···π CH···π interactions strong NH···O H-bonds, which were studied energetically at PBE0-D3/def2-TZVP level theory. Hisrhfeld surface QTAIM analyses NCI plots used to study nature extent different intermolecular in structures, revealing existence additional R21(6) R21(7) synthons. addition, using potential energy density as predictor, method useful investigate relative contribution each interaction assemblies.

Language: Английский

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Visible Light‐Induced Synthesis of Fluorenes from α‐Biaryldiazoacetates

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(8)

Published: Feb. 22, 2024

Abstract Carbenes are pivotal reactive intermediates for accessing a wide range of complex molecules, which frequently used in chemical synthesis and medicinal advancement. We have developed convenient approach to fluorenes from α ‐biaryldiazoacetates via low‐energy blue light‐induced photochemical generation carbene intermediate, where the reaction took place at room temperature without any catalysts, bases, or oxidants acetonitrile. The present catalyst‐free operationally simple enables highly efficient annulation under mild conditions.

Language: Английский

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Reactivity Modulation of Labile Quinones and Biomimetic Catalytic Transformations

Chinese Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 42(3), P. 665 - 665

Published: Jan. 1, 2022

Quinones and their imine counterparts constitute a class of highly electrophilic dearomatized synthon.Their preparation synthetic applications are challenged by limited stability due to the tendency dimerization/polymerization hydrolysis.By taking biomimetic catalytic oxidation strategy, we have developed systems comprising metal catalysts green terminal oxidants that realized in situ phenols reactivity modulation labile quinone intermediates.This has led establishment several [3＋2], [3＋3] [4＋2] cycloadditions control regioselectivity stereoselectivity.In this account, our recent advances quinones/quinone imines transformations summarized.

Language: Английский

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Synthesis and X-Ray Characterization of Two New 1,4-Benzoxazine Derivatives: Structural Analysis and Dft Calculations

Published: Jan. 1, 2024

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Language: Английский

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