Synthesis, Reactions and Antibacterial Activity of 3-Acetyl[1,2,4]triazolo[3,4-a]isoquinoline Derivatives using Chitosan as Heterogeneous Catalyst under Microwave Irradiation

Abstract

3-Acetyl[1,2,4]triazolo[3,4-a]isoquinolines were prepared using chitosan as a catalyst. These compounds were used to prepare a novel series of enaminones 5, and their reactions with hydrazonoyl halides 1 and 11 gave triazoloisoquinolines 8 and 13, respectively, with a carbonylpyrazole side chain. Hydrazinolysis of 8 and 13 gave the pyrazolopyridazines 10 and pyrazolopyridazinones 14. Reaction of 5 with hydroximoyl halides 15 led to triazoloisoquinoline 16 with a carbonylisoxazole side chain. Antibacterial effects of compounds 8 and 10 were studied.

Reactivity of 1-methylisoquinoline synthesis of pyrazolyl triazoloisoquinoline and thia-diazolyl isoquinoline derivatives

“…The presence of such signal is compatible with the assigned structure 4. Indeed the proton resonance of the moiety -N = C(CH 3 )-appears in the 1 H NMR spectra of the dipolarophile 1 at δ 2.3 ppm [23]. This resonance was shifted to higher field in the 1 H NMR spectra (2.08 ppm) of the cycloadducts 4 indicating the conversion of such moiety to the saturated moiety -N-C(CH 3 )-due to cycloaddition.…”

Cytotoxic Activity, Apoptosis Induction and Cell Cycle Arrest in Human Breast Cancer (MCF7) Cells by a Novel Fluorinated Tetrahydro-[1,2,4]Triazolo[3,4-a]Isoquinolin Chalcones

“…To expand our previous ndings in the context of our interest in C-C bond formation reactions [11][12][13], as well as in the synthesis of bioactive compounds [14][15][16][17][18], we synthesized herein a novel series of halogenated chalcones and evaluated their cytotoxic activities against cancer cells. Claisen-Schmidt condensation of 3-acetyl-1-aryltetrahydro- [1,2,4]triazolo [3,4-a]isoquinoline 1 [19,20] with the mole equivalents of 4-uorobenzaldehyde 2 in the presence of 20% KOH solution as a basic catalyst resulted in the formation of the corresponding uorinated [1,2,4]triazolo [3,4-a]isoquinoline chalcones 3-8 (Scheme 1). The constitutions of the synthesized chalcones were con rmed by examining their spectral data.…”

Novel eco-friendly [1,2,4]triazolo[3,4-a]isoquinoline chalcone derivatives efficiency against fungal deterioration of ancient Egyptian mummy cartonnage, Egypt

“…The starting 3-acetyl-8,9-dimethoxy-1-phenyl-1,5,6,10b-tetrahydro-[1,2,4]triazolo[3,4- a ]isoquinoline 1 was obtained following the reported procedures via the reactions of 3,4-dihydro-6,7-dimethoxyisoquinoline with nitrilimines (Elwan et al 1996 ; Hassaneen et al 2011 ). Claisen–Schmidt condensation of compound acetyl compound 1 with the mole equivalents of substituted aldehydes 2 in the presence of potassium hydroxide solution at room temperature affords of the corresponding chalcone derivatives 3–10 (Scheme 1 ).…”