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Synthesis 2024; 56(02): 243-266
DOI: 10.1055/s-0043-1763601
DOI: 10.1055/s-0043-1763601
paper
Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs
The study was funded by a grant from the Russian Science Foundation, No. 22-13-00185, https://rscf.ru/en/project/22-13-00185/. Within the framework of the grant agreement, data on literature analysis, synthesis research procedures, molecular spectra examination, and elemental microanalysis were executed.
Dedicated to the Peace that must return once again.
Abstract
On the basis of the selective reactions of hydrazines with trialkylsilyl-substituted cross-conjugated enynones (pent-1-en-4-yn-3-ones) as fundamental building blocks, this work presents the developed common methodology for the synthesis of polysubstituted luminescent derivatives of acetylenic pyrazolines, pyrazoles, and combined polyheterocycles containing structural fragments from pyrazolines, isoxazoles, thiophenes, thiazoles, benzo[d]thiazoles, and benzo[d]imidazoles. In reactions with hydrazine and its monosubstituted aromatic and heteroaromatic derivatives, the mentioned pent-1-en-4-yn-3-ones, containing Me3Si, Et3Si, and t-BuMe2Si groups at the triple bond, give 3-(trialkylsilyl)ethynylpyrazolines. Following stages of desilylation and 1,3-dipolar cycloaddition with nitrile oxides, the 3-(trialkylsilyl)ethynylpyrazolines provide the formation of combined polyheterocyclic derivatives. Thus, a one-pot synthetic route to pyrazoline-containing isoxazoles from cross-conjugated enynones, arylhydrazines, and α-chlorobenzaldoximes has been developed. Some aspects of cyclocondensation mechanism and luminescent properties of synthesized azoles derivatives were examined.
Key words
trialkylsilyl-substituted conjugated enynones - cyclocondensation - chemoselectivity - desilylation - reaction mechanism - polyheterocycles - luminescence - one-pot synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1763601.
- Supporting Information
Publication History
Received: 07 August 2023
Accepted after revision: 04 October 2023
Article published online:
13 November 2023
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