Recent advances in the synthesis of trifluoromethyl-containing heterocyclic compounds via trifluoromethyl building blocks

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(31), С. 6246 - 6276

Опубликована: Янв. 1, 2024

Recent advances in the preparation of trifluoromethyl-containing heterocyclics via trifluoromethyl building block strategies over period from 2019 to present are systematically summarized and discussed.

Язык: Английский

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Organocatalytic asymmetric cascade bicyclization: access to chiral polycyclic bisindoles from 2-indolylmethanols and propargylic alcohols

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(7), С. 2040 - 2046

Опубликована: Янв. 1, 2024

A chiral phosphoric acid-catalyzed asymmetric bis-cyclization of α-indolyl propargylic alcohols with 2-indolylmethanols was realized.

Язык: Английский

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Chemodivergent (4 + 3) cycloadditions of 2-indolylmethanols with 1,3,5-triazinanes: access to polycyclic indoles

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(13), С. 3624 - 3629

Опубликована: Янв. 1, 2024

Reported herein are the chemodivergent (4 + 3) cycloadditions of 2-indolylmethanols with 1,3,5-triazinanes.

Язык: Английский

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HFIP-Promoted Divergent Cycloadditions of Difluoroenoxysilanes with 2-Indolylmethanols: Synthesis of Fluoro 2H-Pyrano[3,4-b]indoles and gem-Difluoro Cyclopenta[b]indoles

Organic Letters, Год журнала: 2024, Номер 26(22), С. 4610 - 4615

Опубликована: Май 23, 2024

An oxa-6π-electrocyclization of difluoroenoxysilanes with diaryl 2-indolylmethanols has been developed. In addition, a rarely reported C3-nucleophilic [3+2] cycloaddition dialkyl disclosed. This divergent approach affording readily available as three-atom and C2 synthons provides rapid access to fluoro 2

Язык: Английский

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Catalytic asymmetric formal (2 + 3) cycloaddition involving methyl-substituted 2-indolylmethanols

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(17), С. 4812 - 4819

Опубликована: Янв. 1, 2024

A catalytic asymmetric formal (2 + 3) cycloaddition of methyl-substituted 2-indolylmethanols was established, which delivered various chiral pyrroloindoles in overall high yields with excellent diastereoselectivities and good enantioselectivities.

Язык: Английский

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Substrate Controlled [3+3] Relay Catalytic Cyclization of α‐(3‐Isoindolinonyl) Propargylic Alcohols with 5‐Aminoisoxazoles

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

Опубликована: Март 12, 2024

Abstract Two different skeletons have been constructed by cyclization of α‐(3‐isoindolinonyl) propargylic alcohols with 5‐aminoisoxazoles bearing N ‐substituents under the relay catalysis Brønsted acid and Lewis acid. This method provided spiro‐isoindolinone‐dihydropyridines moderate to high yields (up 99 %) as well isoxazolo[4,5‐b]pyridines in good 86 %). The structures two products were determined X‐ray crystal structural analyses. Moreover, fluorescence testing proved that one exhibited aggregation induced emission (AIE) effect. Finally, control experiments revealed possible reaction mechanism.

Язык: Английский

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Enantioselective intramolecular tandem cyclization of o-alkynylbenzamides: generation of enantioenriched CF₃-containing spiro-isoindolinone-indoles

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(9), С. 2591 - 2599

Опубликована: Янв. 1, 2024

Enantioselective intramolecular tandem cyclization of dielectrophile–dinucleophile assembled o -alkynylbenzamides provided a variety spiro-isoindolinone-indoles in low to moderate yields with good enantioselectivities.

Язык: Английский

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Synthesis of Chiral 3H‐pyrrolo[1,2‐a]indoles via Organocatalytic Enantioselective Addition of Alkynyl Biphenyl Quinone Methides

ChemCatChem, Год журнала: 2024, Номер 16(21)

Опубликована: Июль 17, 2024

Abstract An organocatalytic enantioselective reaction utilizing α‐[4‐(4‐hydroxyphenyl)phenyl]propargyl alcohols and 3‐substituted indoles has been successfully established for the synthesis of chiral 3 H ‐pyrrolo[1,2‐ a ]indoles. Through assistance an appropriate phosphoric acid, cascade sequence is facilitated, beginning with dehydration to form alkynyl 4,4’‐biphenyl quinone methides ( 4,4’‐BQMs ). Subsequently, 1,12‐addition ]indoles these results in formation allenes, which are then protonated regenerate . Finally, intramolecular annulation occurs smoothly, leading production range high efficiency asymmetric induction.

Язык: Английский

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Lewis-Acid-Catalyzed (3+2) Annulation of 2-Indolylmethanols with Propargylic Alcohols to Access Cyclopenta[b]indoles

Molecules, Год журнала: 2024, Номер 29(6), С. 1251 - 1251

Опубликована: Март 12, 2024

Herein, a Sc(OTf)3-catalyzed (3+2) annulation of 2-indolylmethanols with propargylic alcohols is reported. The reaction proceeds via Friedel–Crafts-type allenylation/5-exo-annulation cascade. In the reaction, 2-indolylmethanol used as three-carbon synthon, and propargyl alcohol two-carbon synthon. This method provides direct high-yield pathway for synthetically useful cyclopenta[b]indoles. general, features easily accessible substrates broad scope generality, formation multiple bonds high efficiency, easy scale-up.

Язык: Английский

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In(OTf)3-Catalyzed Formal (4 + 3) Cycloaddition Reactions of 3-Benzylideneindoline-2-thiones with 2-Indolylmethanols

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(29), С. 5902 - 5906

Опубликована: Янв. 1, 2024

We report the In(OTf)

Язык: Английский

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