Tandem Addition/Cyclization/Halogenation Reaction of Difluoromethylated N-Acylhydrazones with Allyltrimethylsilanes

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(24), P. 17356 - 17367

Published: Dec. 6, 2023

As novel difluoromethyl building blocks, difluoromethylated N-acylhydrazones react with allyltrimethylsilanes and the halogen source via a tandem addition/cyclization/halogenation strategy, which produces various difluoromethylpyrazoline compounds in good yields. The method features mild reaction conditions, broad substrate scopes, transition metal-free process easy operation. It also proves that are useful blocks for construction of nitrogen heterocycles.

Language: Английский

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Synthesis of Difluoromethyl Chromono[3,2-c]pyrazolines/pyrazoles by [3+2] Cycloaddition Reaction of Difluoroacetohydrazonoyl Bromides with 3-EWG-Chromones

Synthesis, Journal Year: 2024, Volume and Issue: 56(22), P. 3475 - 3487

Published: July 18, 2024

Abstract A highly convenient and straightforward strategy for the synthesis of difluoromethyl substituted tricyclic fused chromono[3,2-c]pyrazolines/pyrazoles is developed via [3+2]-cycloaddition difluoroacetohydrazonoyl bromides to chromene derivatives bearing an electron-withdrawing group at 3-position. The reaction has advantages mild conditions, good tolerance functional groups, simple operation.

Language: Английский

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(3+2)-Cycloadditions of Levoglucosenone (LGO) with Fluorinated Nitrile Imines Derived from Trifluoroacetonitrile: An Experimental and Computational Study

Molecules, Journal Year: 2023, Volume and Issue: 28(21), P. 7348 - 7348

Published: Oct. 30, 2023

The in situ-generated N-aryl nitrile imines derived from trifluoroacetonitrile smoothly undergo (3+2)-cycloadditions onto the enone fragment of levoglucosenone molecule, yielding corresponding, five-membered cycloadducts. In contrast to ‘classic’ C(Ph),N(Ph) imine, reactions with fluorinated C(CF3),N(Ar) analogues lead stable pyrazolines a chemo- and stereoselective manner. Based on result X-ray single crystal diffraction analysis, their structures were established as exo-cycloadducts location N-Ar terminus 1,3-dipole at α-position moiety. DFT computation demonstrated that observed reaction pathway results strong dominance kinetic control over thermodynamic control.

Language: Английский

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Divergent synthesis of difluoromethylated indole-3-carbinols, bisindolylmethanes and indole-3-methanamines

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(1), P. 90 - 94

Published: Nov. 24, 2023

A facile and straightforward method for the successful synthesis of difluoromethylated indole-3-carbinols, bisindolylmethanes indole-3-methanamines by a Friedel–Crafts reaction is developed.

Language: Английский

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Five-membered ring systems: with more than one N atom

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 281 - 332

Published: Jan. 1, 2023

Language: Английский

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