Copper-Catalyzed Bisannulations of Malonate-Tethered O-Acyl Oximes with Pyridine, Pyrazine, Pyridazine, and Quinoline Derivatives for the Construction of Dihydroindolizine-Fused Pyrrolidinones and Analogues

Organic Letters, Год журнала: 2021, Номер 23(22), С. 8699 - 8704

Опубликована: Ноя. 1, 2021

A copper-catalyzed bisannulation reaction of malonate-tethered O-acyl oximes with pyridine, pyrazine, pyridazine, and quinoline derivatives has been developed for the concise synthesis structurally novel dihydroindolizine-fused pyrrolidinones their analogues. The present shows excellent regioselectivity stereoselectivity. Theoretical calculations reveal that coordination effect carbonyl group in nucleophilic substrate determines regioselectivity. Further functionalization generated pyrrolidinone could be easily realized through substitution, Michael addition, selective aminolysis, hydrolysis reactions.

Язык: Английский

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Efficient Solvent-Free Synthesis of Indolizines Using CuBr Catalyst from Pyridine, Acetophenone, and Electron-Deficient Alkenes

Molecules, Год журнала: 2024, Номер 29(9), С. 2061 - 2061

Опубликована: Апрель 29, 2024

Herein, we have developed a new approach for the synthesis of indolizine via Cu-catalyzed reaction pyridine, acetophenone, and nitroolefin under mild conditions in high yields. This involved formation C–N C–C bonds compounds with stereoselectivity excellent functional group tolerance.

Язык: Английский

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Oxidative [4+2] Annulation of Pyrrole‐2‐carbaldehyde Derivatives with o‐Hydroxyphenyl Propargylamines: Syntheses of 5,6,7‐Trisubstituted Indolizines

Chemistry - A European Journal, Год журнала: 2024, Номер 30(63)

Опубликована: Авг. 23, 2024

Abstract A base promoted oxidative [4+2] annulation of pyrrole‐2‐carbaldehyde derivatives with o ‐hydroxyphenyl propargylamines for the synthesis highly substituted indolizines has been developed. Using DBN as base, a broad range 5,6,7‐trisubstituted have prepared in good to excellent yields under mild conditions, and many useful functional groups can be tolerated.

Язык: Английский

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Iodine-Mediated Domino Cyclization for One-Pot Synthesis of Indolizine-Fused Chromones via Metal-Free sp³ C–H Functionalization

The Journal of Organic Chemistry, Год журнала: 2021, Номер 87(1), С. 835 - 845

Опубликована: Дек. 28, 2021

An efficient method for the synthesis of new indolizine-fused chromones has been accomplished from ethyl (E)-3-(2-acetylphenoxy)acrylates and pyridines in a "one-pot" manner. Facile operation open-air, metal-free, mild conditions renders this protocol particularly practical attractive. Moreover, can simultaneously construct two molecular fragments chromone indolizine. Scale-up experiment construction natural products further prove practicability strategy.

Язык: Английский

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N-Difluoromethylation of N-pyridyl-substituted anilines with ethyl bromodifluoroacetate

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(9), С. 1883 - 1887

Опубликована: Янв. 1, 2022

A general protocol for N -difluoromethylation of aniline derivatives is developed.

Язык: Английский

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