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

DÜNDAR B. A., ZORA M.

SYNTHETIC COMMUNICATIONS, vol.52, no.3, pp.356-367, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 52 Issue: 3
  • Publication Date: 2022
  • Doi Number: 10.1080/00397911.2021.2024575
  • Journal Name: SYNTHETIC COMMUNICATIONS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, EMBASE
  • Page Numbers: pp.356-367
  • 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
  • Middle East Technical University Affiliated: Yes

Abstract

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.