A facile synthesis of a novel family of heterotricyclic hybrids: Spiro-pyrrolopyridazines

Date

2022-01-01

Author

Dündar, Buse Ayşen
Zora, Metin

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An efficient strategy for the synthesis of spiro-pyrrolopyridazines has been developed. When reacted with hydrazine monohydrate, spiro-2H-pyrroles with a 1,4-diketone functionality produced a novel family of heterotricyclic hybrids, spiro-pyrrolopyridazines, specifically spiro{cyclohexane-1,5'-pyrrolo[3,4-d]pyridazine} systems. The condensation reaction of spiro-2H-pyrroles with hydrazine monohydrate in refluxing 1-butanol proceeded well and afforded spiro-pyrrolopyridazines in good to high yields. The reaction was found to be general for variety of spiro-2H-pyrroles and demonstrated good tolerance to a variety of aromatic and heteroaromatic groups with electron-withdrawing and electron-donating substituents. The synthesis of heterotricyclic spiro-pyrrolopyridazine hybrids may exhibit potential to deliver diverse structural motifs that aid the drug discovery efforts.

Subject Keywords

Pyridazine, pyrrole, 2H-pyrrole, N-propargylic beta-enaminone, spiro compounds, condensation reaction, ONE-POT SYNTHESIS, PROPARGYLIC BETA-ENAMINONES, MEDICINAL CHEMISTRY, PYRIDAZINE, DERIVATIVES, DRUG, IRBESARTAN, DISCOVERY, FLUORINE, POLYMERS

URI

https://hdl.handle.net/11511/95407

Journal

SYNTHETIC COMMUNICATIONS

DOI

https://doi.org/10.1080/00397911.2021.2024575

Collections

Department of Chemistry, Article

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Citation Formats

B. A. Dündar and M. Zora, “A facile synthesis of a novel family of heterotricyclic hybrids: Spiro-pyrrolopyridazines,” SYNTHETIC COMMUNICATIONS, pp. 0–0, 2022, Accessed: 00, 2022. [Online]. Available: https://hdl.handle.net/11511/95407.