Synthesis of 6H-Benzo[c]chromene Scaffolds: A Synthetic Strategy of Pd-Catalyzed Annulation Followed by Aerial Oxidation

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 3, 2025

A synthetic strategy of a palladium-catalyzed cascade annulation reaction followed by aerial oxidation was designed to construct 6H-benzo[c]chromene scaffolds. Various 6H-benzo[c]chromenes were synthesized under mild conditions using easily accessible p-QMs and commercially available o-hydroxyarylboronic acids. One the chromenes has been ambiguously confirmed single-crystal XRD analysis. Interestingly, our could be transformed into valuable 6H-benzo[c]chromen-6-ones via oxidation.

Language: Английский

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Construction of Oxygen‐ and Nitrogen‐based Heterocycles from p‐Quinone Methides

The Chemical Record, Journal Year: 2021, Volume and Issue: 21(12), P. 4150 - 4173

Published: Aug. 9, 2021

In the last few years, there has been an explosive growth in area of para-quinone methide (p-QM) chemistry. This boom is actually due to unique reactivity pattern p-QMs, and also their remarkable synthetic applications. fact, p-QMs serve as synthons for unsymmetrical diaryl- triarylmethanes, construction diverse range carbocycles heterocycles. a wide structurally complex heterocyclic frameworks could be accessed through transformations modified stable p-QMs. Therefore, main focus this review article cover recent advancements transition-metal, Lewis acid base-catalyzed/mediated p-quinone methides (p-QMs) oxygen- nitrogen-containing

Language: Английский

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Design and Application of m‐Hydroxybenzyl Alcohols in Regioselective (3 + 3) Cycloadditions of 2‐Indolymethanols^†

Chinese Journal of Chemistry, Journal Year: 2022, Volume and Issue: 41(1), P. 27 - 36

Published: Sept. 16, 2022

Comprehensive Summary A new class of m ‐hydroxybenzyl alcohols has been designed as competent three‐carbon building blocks and achieved their application in 2‐indolylmethanol‐involved regioselective (3 + 3) cycloadditions under the catalysis Brønsted acids. By this appoach, a series indole‐fused six‐membered cycloadducts have synthesized overall good yields (up to 98%) with excellent regioselectivity (all >95: 5 rr), thus affording powerful method for construction rings. Moreover, catalytic asymmetric version cycloaddition preliminarily investigated, which revealed potential reaction constructing chiral rings an enantioselective manner. This work not only accomplished first design reactants, but also represents cycloadditions. In addition, provides example C3‐nucleophilic 2‐indolylmethanols, will substantially enrich chemistry 2‐indolylmethanols.

Language: Английский

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Recent Advances in Stimuli-Responsive Self-Immolative Polymers for Drug Delivery and Molecular Imaging

Chemistry of Materials, Journal Year: 2024, Volume and Issue: 36(9), P. 4054 - 4077

Published: April 18, 2024

Stimuli-responsive self-immolative polymers (SIPs) represent a unique class of that can undergo controlled, sequential head-to-tail depolymerization upon specific stimuli. Since their inception, they have evolved over two decades to become one the most attractive polymer types. With characteristic feature "one stimulus, multiple responses", SIPs inherently possess ability serve as chemical amplifiers, which amplify weak or biological signals. This promises higher stimulus sensitivity, greater selectivity for microenvironments, and potential generate more persistent, extensive, significant responses while consuming fewer stimuli sources. Review summarizes latest research advancements in stimuli-responsive drug delivery molecular imaging past five years. Regarding structure SIPs, we briefly overview updates self-immolation units, end-cap moieties, sequence SIPs. In terms applications, focus on possible applications disease treatment methods. Finally, provide brief perspective future directions these applications.

Language: Английский

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Design and Development of Carbene-Catalyzed Intramolecular Vinylogous Stetter Reaction to Access Phenanthrol Derivatives

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 4, 2025

The present study reveals the design and development of an N-heterocyclic carbene (NHC)-catalyzed intramolecular vinylogous Stetter reaction. This protocol enabled synthesis diverse phenanthrol derivatives naphthol-fused heterocycles in very good to excellent yields. success title reaction relies on biaryl aldehydes bearing p-quinone methide (p-QM) moiety that acts as a (1,6-conjugate) acceptor while aldehyde functional group serves acyl anion equivalent, generated situ from NHC-catalyzed umpolung. Salient features presented include atom efficiency, operational simplicity, broad substrate scope, large-scale synthesis, postsynthetic modifications.

Language: Английский

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Visible light and base promoted O-H insertion/cyclization of para-quinone methides with aryl diazoacetates: An approach to 2,3-dihydrobenzofuran derivatives

Chinese Chemical Letters, Journal Year: 2021, Volume and Issue: 32(8), P. 2577 - 2581

Published: March 7, 2021

Language: Английский

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Engaging Yne‐Allenes in Cycloaddition Reactions: Recent Developments

Chinese Journal of Chemistry, Journal Year: 2022, Volume and Issue: 40(10), P. 1224 - 1242

Published: Jan. 26, 2022

Comprehensive Summary Yne‐allenes bearing both a C—C triple bond and an allene unit are class of focal substrates in organic synthesis, view their structure diversity, high reactivity intermediate variety the past years. Engaging yne‐allenes numerous annulation cascades provides efficient direct accesses to elaborate functionalized polycyclic molecular architectures convergent manner. There lots types catalytic chemical reactions such as intramolecular cyclizations, cycloisomerizations, intermolecular annulations, bicyclizations well tricyclizations with assistance Lewis acids, Brønsted bases, transition metals, other catalysts. This review overview chemistry developed transformations by discussing general specific reactivities, presenting commenting on mechanisms applications.

Language: Английский

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Organocatalytic Enantioselective 1,10-Addition of Alkynyl Indole Imine Methides with Thiazolones: An Access to Axially Chiral Tetrasubstituted Allenes

Organic Letters, Journal Year: 2022, Volume and Issue: 24(27), P. 4914 - 4918

Published: June 30, 2022

An asymmetric organocatalytic remote 1,10-addition of alkynyl indole imine methides generated in situ from α-(6-indolyl) propargylic alcohols with thiazolones has been developed for the first time, affording axially chiral tetrasubstituted allenes featuring vicinal sulfur-containing quaternary carbon stereocenters high yields excellent stereoselectivities. The representative scale-up reaction and transformations 1,10-adduct were examined. mechanism was expounded by control experiments DFT calculations.

Language: Английский

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Merging dearomatization with redox-neutral C(sp³)–H functionalization via hydride transfer/cyclization: recent advances and perspectives

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(18), P. 5041 - 5052

Published: Jan. 1, 2022

This review highlights the encouraging advances in hydride transfer-involved dearomatization reaction during past decade, content of which is categorized according to acceptors, namely vinylogous imines and quinone methides.

Language: Английский

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Chiral Brønsted acid-catalyzed asymmetric intermolecular [4 + 2] annulation of ynamides with para-quinone methides

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(5), P. 1467 - 1473

Published: April 12, 2023

Language: Английский

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