[3,3] Ring Rearrangement of Oxo- or Aza-Bridged Bicyclo[3.2.1]octene-Based 1,5-Dienes

Organic Letters, Год журнала: 2021, Номер 23(6), С. 2263 - 2267

Опубликована: Март 10, 2021

We report that oxo- or aza-bridged alkylidenemalononitrile-cycloheptenes undergo a [3,3] ring rearrangement to yield cyclopenta-fused dihydro-furans pyrroles. Described herein are the origins of serendipitous discovery, scope studies, and representative functional group interconversion chemistry.

Язык: Английский

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Methyl (2E)-3-[3-Benzyl-2-(3-methoxy-3-oxoprop-1-yn-1-yl)-2-(1-naphthyl)imidazolidin-1-yl]acrylate

Molbank, Год журнала: 2020, Номер 2021(1), С. M1176 - M1176

Опубликована: Дек. 30, 2020

Compounds with propargylamine moiety are useful synthetic precursors of several important classes nitrogen-containing heterocycles. The title compound, methyl (2E)-3-[3-benzyl-2-(3-methoxy-3-oxoprop-1-yn-1-yl)-2-(1-naphthyl)imidazolidine-1-yl]acrylate, has been prepared by domino-reaction, employing easily available 1-benzyl-2-(1-naphthyl)-4,5-dihydro-1H-imidazole and propiolate in a high 92% yield. structure compound was determined using 1H-NMR, 13C-NMR, UV, FT-IR HRMS (High-Resolution Mass Spectrometry).

Язык: Английский

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Domino synthetic strategy for tetrahydrothiophene derivatives from 2-acetylfuran/2-acetylthiophene, benzaldehydes, and sulfur powder

Arabian Journal of Chemistry, Год журнала: 2022, Номер 15(9), С. 104097 - 104097

Опубликована: Июль 7, 2022

A domino reaction from 2-acetylfuran/2-acetylthiophene, benzaldehydes and sulfur powder has been developed to synthesize a series of tetrahydrothiophene derivatives. The proceeds well construct five new bonds ring by one-pot. possible mechanism was proposed, involving stepwise Aldol/double Michael addition/internal SN2 cascaded with acts as source sulfur. This method is characterized mild conditions, commercially available starting materials transition-metal-free.

Язык: Английский

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Tracking the Process of Domino Ring‐Opening and Coupling of Fused Imidazole and Direct Observation of Peroxide Intermediates

Chinese Journal of Chemistry, Год журнала: 2023, Номер 41(17), С. 2089 - 2094

Опубликована: Май 8, 2023

Comprehensive Summary A domino ring‐opening and coupling of imidazolyl annulated heterocycles 1 ( 1a : 4‐methyl‐1‐(1‐methyl‐1 H ‐benzo[ d ]imidazol‐2‐yl)‐4 ‐ benzo[ ]imidazo[1,5‐ a ]imidazole, 1b 1‐(1,5‐dimethyl‐1 ]imidazol‐2‐yl)‐4,7‐dimethyl‐4 ]imidazole) with dioxygen was developed at solvothermal condition, leading to conjugated 1,2‐diamidoalkenes derivatives 2 (( E )‐ArCONHArC=CArNHCOAr (Ar: 1‐methyl‐1 ]imidazolyl 2a ), 1,5‐dimethyl‐1 2b ))) as single crystals directly. The reaction process tracked by electrospray ionization mass spectrometry (ESI‐HRMS) series intermediates are detected. 18 O labeling experiment verified the source oxygen in . Combining evidence from control experiments, nuclear magnetic resonance (NMR) tracking, crystallography, seven‐step pathway involving addition, ring opening, Friedel‐Crafts alkylation, oxidation, dehydration proposed further supported DFT calculation.

Язык: Английский

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Green synthesis of polysubstituted pyrroles through a domino sequence of aza-Claisen rearrangement/nucleophilic addition/oxidation/acylation

AIP conference proceedings, Год журнала: 2022, Номер 2390, С. 020019 - 020019

Опубликована: Янв. 1, 2022

A pseudo three-component reaction of 2-imidazolines with electron-deficient alkynes furnishes 1,2,2,3-tetrasubstituted imidazolidines containing N-vinylpropargylamine moiety. Heating in aerobic conditions butyl acetate solution leads to highly functionalized pyrroles through aza-Claisen rearrangement/nucleophilic addition/oxidation/acylation.

Язык: Английский

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