The first synthesis of furo[2,3- c ]pyridazin-4(1 H )-one derivatives

Kelemen, Ádám Andor; Szabó, Balázs; Kovács, P.; Keserü, György M.

doi:10.1016/j.tetlet.2015.11.068

Cited by 5 publications

(2 citation statements)

References 10 publications

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“…In the synthetic strategy, the authors used a LDAmediated cyclization reaction on arylhydrazones derivatives 14 synthesized in five steps from furan-3-carboxylic acid 13. 23 The cyclization step was performed using LDA as lithiation reagent providing furo[2,3-c]pyridazin-4(1H)ones 15 in good yields albeit with limited range of substituents (Scheme 5). No exploitation of this new ring system in drug discovery projects has been reported so far.…”

Section: Furo[23-c]pyridazin-4(1h)-one-p5mentioning

confidence: 99%

‘Heteroaromatic Rings of the Future’: Exploration of Unconquered Chemical Space

Passador

Thorimbert

Botuha³

2018

Synthesis

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William Pitt and co-workers have created a virtual exploratory heterocyclic library ‘VEHICLe’ containing over 200 unconquered bicyclic heteroaromatic rings, synthetically feasible with potential medicinal interest. Since the publication of the 22 ‘heteroaromatic rings of the future’ by Pitt in 2009, 15 of them have been successfully synthesized as bicyclic or polycyclic forms and evaluated for applications in both biology and material science. This short review presents the critical synthesis associated with innovative synthetic methodologies of the synthetically conquered ring scaffolds from the list of 22 with a spotlight on the scientific contribution of this fascinating article for the expansion of the chemical diversity.1 Introduction2 Heteroaromatic Rings of the Future: The Synthetic challenge?2.1 4-Pyrido[1,3]oxazin-4-one-P1 2.2 Pyrrolo[2,1-b][1,3]oxazin-4-one-P4 2.3 Furo[2,1-e]pyridazin-4(1H)-one-P5 2.4 Isoxazolo[3,4-c]pyridin-7-one-P6 2.5 5H,6H-[1,2]Thiazolo[5,4-c]pyridin-5-one-P7 2.6 4H,5H-Furo[3,2-b]pyridin-5-one-P8 2.7 1H,5H,6H-Pyrazolo[3,4-c]pyridin-5-one-P9 2.8 Thieno[3,4-c]pyridazine-P10 2.9 Pyrrolo[1,2-c][1,2,3]triazine-P11 2.10 Thieno[3,4-a]oxazole-P12 2.11 2,4-Dihydropyrrolo[3,2-c]pyrazole-P13 2.12 Pyrazolo[1,5-b]isoxazole-P14 2.13 Imidazo[1,5-c]pyrimidin-3(2H)-one-P16 2.14 Cyclopenta[b][1,4]oxazin-5(4H)-one-P17 2.15 2,3-Dihydro-2,6-naphthyridin-3-one-P18 3 Conclusion

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Section: Furo[23-c]pyridazin-4(1h)-one-p5mentioning

confidence: 99%

‘Heteroaromatic Rings of the Future’: Exploration of Unconquered Chemical Space

Passador

Thorimbert

Botuha³

2018

Synthesis

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“…To date, rarely straightforward methods for the synthesis of pyridazin-4(1 H )-ones and oxazin-4(1 H )-ones have been developed, mainly including the C1 insertion of diazo compound with DMFDMA ( N , N -dimethyl for mamide dimethyl acctel) simultaneous cyclization reaction (Scheme a). , ortho -Ethynylated aniline derivatives undergo intramolecular cyclization with the formation of cinnolines under Richter reaction (Scheme b) . Despite making corresponding progress, there are still some issues such as the diazo reagents generated in the reaction process and the toxicity of the sodium nitrite molecules leading to multiple side reactions.…”

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confidence: 99%

Oxygen-Promoted 6-endo-trig Cyclization of β,γ-Unsaturated Hydrazones/Ketoximes with Diazonium Tetrafluoroborates for Pyridazin-4(1H)-ones/Oxazin-4(1H)-ones

Wen

Zhao

et al. 2023

Org. Lett.

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An oxidative 6-endo-trig cyclization and [2 + 2] cycloaddition of β,γ-unsaturated hydrazones/ketoximes and diazonium tetrafluoroborates for a synthetic strategy to pyridazin-4(1H)-ones/oxazin-4(1H)-ones under metal-free conditions is presented in a one-pot procedure. This protocol features excellent functional group tolerance and remarkable regioselectivity. A mechanistic study has been verified via 18 O labeling and the H 2 18 O labeling method, in which O 2 acts as both a reaction component and an oxidant. P yridazin-ones and oxazin-ones scaffolds, which contain two adjacent heteroatoms in the ring and one carbonyl group, are commonly found in a wide range of bioactive compounds, 1 pharmaceutical molecules, 2 functional materials, 3 and rarely natural products. 4 Among them, Pyridazin-4(1H)one and oxazin-4(1H)-one derivatives have gained tremendous attention because of their applications in the pharmacological properties such as antihypertensive, antinociceptive, antibacterial, antifungal, analgesic, anticancer, and inhibition activities (Figure 1). 5 However, due to the lack of suitable synthetic

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