N‑Alkylated 1,4-Diazabicyclo[2.2.2]octane–Polyethylene Glycol Melt as Deep Eutectic Solvent for the Synthesis of Fisher Indoles and 1<i>H</i>‑Tetrazoles

1,4-Diazabicyclo­[2.2.2]­octane (DABCO)-based ionic liquids (ILs) <b>2–4</b> were synthesized by the N-alkylation of DABCO using alkyl halides of varying chain lengths (C₂, C₅, and C₇). The N-alkylated DABCO-ILs were mixed with polyethylene glycols (PEGs) of varying molar masses as hydrogen bond donors (HBDs) to prepare new deep eutectic solvents (DESs). These DABCO–PEG-based DESs were successfully employed for the synthesis of a variety of indoles <b>7a–7h</b> (by Fischer indole synthesis) and 1<i>H</i>-tetrazoles <b>9a–9i</b> (by click chemistry). For comparison, DESs of DABCO-ILs with different alcohols (as HBD) were also prepared and investigated for the synthesis of indoles. Although comparable yields were observed in DES-containing alcohols and PEGs, the use of PEG as HBD in DES (as an alternative to alcohols) provides a much safer, nonvolatile, and environmentally benign reaction medium for synthetic reactions. The first successful application of PEG-polymer-based DES as benign reaction media for organic syntheses offers exciting opportunities to be explored in the realm of green synthesis

DABCO–PEG ionic liquid-based synthesis of acridine analogous and its inhibitory activity on alkaline phosphatase

<p>In world, many people struggle with viral, parasitic, bacterial, cancer, and other diseases. Therefore, numerous chemists seek to develop less toxic, more selective, and effective medicines. Most therapeutic medicines are based on inhibition of specific enzymes. Acridines are interesting heterocyclic structures that are much sought after targets attributed to their wide biological activities and feature to display potent enzymes inhibitory effects. Their approach of action is owing to DNA interaction and subsequent effects on the biological functions linked to DNA and associated enzymes. In this regards, we synthesized acridine analogous through 1,4-diazabicyclo[2.2.2]octane (DABCO)–polyethylene glycol-400 (PEG-400) mediated ionic liquid approach. DABCO–PEG-400-mediated IL was prepared through the DABCO alkylation using 1-bromopentane followed by mixing with PEG-400. The synthesized analogous were investigated as inhibitors of alkaline phosphatase, which is a nonspecific phosphomonoester hydrolase that catalyzes the hydrolysis of broad spectrum of organic monophosphates. Analogue viz. 3,3,6,6-tetramethyl-9-(4-nitrophenyl)-2,3,4,5,6,7,9,10-octahydroacridine-1,8-dione was found to be potent alkaline phosphatase inhibitor.</p