Catalyst-Free Assembly of δ-Lactam-Based Hydrazide–Hydrazone Compounds from 3-Arylglutaconic Anhydrides and Aldazines

Ananeva, Anna; Karchuganova, Elizaveta; Spiridonova, Dar’ya; Kantin, Grigory; Bakulina, Olga

doi:10.3390/ijms26188834

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Catalyst-Free Assembly of δ-Lactam-Based Hydrazide–Hydrazone Compounds from 3-Arylglutaconic Anhydrides and Aldazines

by

Anna Ananeva

,

Elizaveta Karchuganova

,

Dar’ya Spiridonova

,

Grigory Kantin

and

Olga Bakulina

^*

Department of Medicinal Chemistry, Institute of Chemistry, Saint Petersburg State University, 199034 Saint Petersburg, Russia

^*

Author to whom correspondence should be addressed.

Int. J. Mol. Sci. 2025, 26(18), 8834; https://doi.org/10.3390/ijms26188834

Submission received: 24 July 2025 / Revised: 30 August 2025 / Accepted: 2 September 2025 / Published: 10 September 2025

(This article belongs to the Special Issue Synthesis and Application of Natural and Inspired-Natural Products)

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Abstract

A novel general approach to cyclic hydrazide–hydrazone compounds with a dihydropyridine-2-one core has been developed, involving annulation of symmetrical aldazines with 3-arylglutaconic anhydrides. This approach provides the benefits of straightforward and catalyst-free procedures, diastereoselectivity, and the ability to switch between two isomeric dihydropyridine-2-one cores based on the reaction temperature. Several post-modifications were performed on the side functional groups and the core to demonstrate the synthetic potential of the resulting products. This approach significantly expands the chemical diversity of medicinally relevant N-functionalized δ-lactams.

Keywords: hydrazide–hydrazone; aldazine; anhydride; arylglutaconic; δ-lactam; annulation

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MDPI and ACS Style

Ananeva, A.; Karchuganova, E.; Spiridonova, D.; Kantin, G.; Bakulina, O. Catalyst-Free Assembly of δ-Lactam-Based Hydrazide–Hydrazone Compounds from 3-Arylglutaconic Anhydrides and Aldazines. Int. J. Mol. Sci. 2025, 26, 8834. https://doi.org/10.3390/ijms26188834

AMA Style

Ananeva A, Karchuganova E, Spiridonova D, Kantin G, Bakulina O. Catalyst-Free Assembly of δ-Lactam-Based Hydrazide–Hydrazone Compounds from 3-Arylglutaconic Anhydrides and Aldazines. International Journal of Molecular Sciences. 2025; 26(18):8834. https://doi.org/10.3390/ijms26188834

Chicago/Turabian Style

Ananeva, Anna, Elizaveta Karchuganova, Dar’ya Spiridonova, Grigory Kantin, and Olga Bakulina. 2025. "Catalyst-Free Assembly of δ-Lactam-Based Hydrazide–Hydrazone Compounds from 3-Arylglutaconic Anhydrides and Aldazines" International Journal of Molecular Sciences 26, no. 18: 8834. https://doi.org/10.3390/ijms26188834

APA Style

Ananeva, A., Karchuganova, E., Spiridonova, D., Kantin, G., & Bakulina, O. (2025). Catalyst-Free Assembly of δ-Lactam-Based Hydrazide–Hydrazone Compounds from 3-Arylglutaconic Anhydrides and Aldazines. International Journal of Molecular Sciences, 26(18), 8834. https://doi.org/10.3390/ijms26188834

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Catalyst-Free Assembly of δ-Lactam-Based Hydrazide–Hydrazone Compounds from 3-Arylglutaconic Anhydrides and Aldazines

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