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Thiocyanate-induced N-activation and nucleophilic 1,2-dearomatization of pyridinedicarbonyl dichloride: a synthetic route to a novel 1,2-dihydropyridine-based heterocyclic compound


Mukiza, Janvier; Habarurema, Gratien; Nkuranga, Jean Bosco; Sezirahiga, Jurdas; Akin-Ojo, Omololu; Nkurunziza, Jean Baptiste; Kampire, Edwidge; Gakuba, Emmanuel; Blacque, Olivier (2023). Thiocyanate-induced N-activation and nucleophilic 1,2-dearomatization of pyridinedicarbonyl dichloride: a synthetic route to a novel 1,2-dihydropyridine-based heterocyclic compound. Journal of the Iranian Chemical Society, 20(10):2657-2664.

Abstract

The 1,2-dearomatized pyridine derivatives are among the most beneficial scaffolds for synthetic and medicinal chemistry and have along with others substantially contributed to pharmaceutical research. We report uncatalyzed thiocyanate-induced N-activation and nucleophilic 1,2-dearomatization of pyridinedicarbonyl dichloride with further addition of diphenylamine leading to the novel 1,2-dihydropyridine-based heterocyclic compound; ( +/-) 2 '-(diphenylamino)-3-thioxo-2,3-dihydro-1H,4 ' H-spiro[imidazo[1,5-a]pyridine-5,5 '-thiazole]-1,4 '-dione (1). The previously reported dearomatizations of pyridine and its derivatives usually demand a specific catalyst. Therefore, uncatalyzed 1,2-dearomatization of pyridinedicarbonyl dichloride observed in this study is unusual. Heterocyclic compound 1 will act as potential mother reagent for the synthetic route to a variety of novel heterocyclic compounds derivative to 1,2-dihydropyridine. The purity of the product was assessed by Ultraperformance Liquid Chromatography (UPLC), and the structural characterization was achieved by H-1 NMR, C-13 NMR, DEPT-135-NMR, IR, Liquid Chromatography Mass Spectrometry (ESI-MS), single crystal X-ray crystallography and density function theory (DFT).

Abstract

The 1,2-dearomatized pyridine derivatives are among the most beneficial scaffolds for synthetic and medicinal chemistry and have along with others substantially contributed to pharmaceutical research. We report uncatalyzed thiocyanate-induced N-activation and nucleophilic 1,2-dearomatization of pyridinedicarbonyl dichloride with further addition of diphenylamine leading to the novel 1,2-dihydropyridine-based heterocyclic compound; ( +/-) 2 '-(diphenylamino)-3-thioxo-2,3-dihydro-1H,4 ' H-spiro[imidazo[1,5-a]pyridine-5,5 '-thiazole]-1,4 '-dione (1). The previously reported dearomatizations of pyridine and its derivatives usually demand a specific catalyst. Therefore, uncatalyzed 1,2-dearomatization of pyridinedicarbonyl dichloride observed in this study is unusual. Heterocyclic compound 1 will act as potential mother reagent for the synthetic route to a variety of novel heterocyclic compounds derivative to 1,2-dihydropyridine. The purity of the product was assessed by Ultraperformance Liquid Chromatography (UPLC), and the structural characterization was achieved by H-1 NMR, C-13 NMR, DEPT-135-NMR, IR, Liquid Chromatography Mass Spectrometry (ESI-MS), single crystal X-ray crystallography and density function theory (DFT).

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Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > General Chemistry
Uncontrolled Keywords:General Chemistry
Language:English
Date:1 October 2023
Deposited On:19 Jan 2024 14:26
Last Modified:30 Jun 2024 01:37
Publisher:Iranian Chemical Society
ISSN:1735-207X
OA Status:Closed
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1007/s13738-023-02863-1
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