Heteroannulated pyranoquinolinediones: Part 1. An efficient and convenient synthesis of the novel heteroannulated pyrano[3,2-c] quinoline-2,5(6H)-diones

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The starting compound 2‐hydrazinyl‐7‐(4‐methoxyphenyl)‐5‐oxo‐3,5‐dihydro[1,2,4]triazolo[1,5‐a]pyridine‐6,8‐dicarbonitrile (5) was efficiently synthesized from 1,6‐diamino‐4‐(4‐methoxyphenyl)‐2‐oxo‐1,2‐dihydropyridine‐3,5‐dicarbonitrile (1). A novel series of polynuclear [1,2,4]triazolo[4′,3′:2,3][1,2,4]triazolo[1,5‐a]pyridines 6, 7, 8, 9, 10 and pyrido[1′,2′:2,3][1,2,4]triazolo[5,1‐c][1,2,4]triazines 11, 12, 13, 14, 15 have been synthesized. Structures of the newly synthesized products have been deduced on the basis of elemental analysis and spectral data. The synthesized compounds were screened for their antimicrobial activity.

Synthesis, Characterization, and Antimicrobial Evaluation of the Novel Triazolotriazolopyridines and Pyridotriazolotriazines

El-Kazak

Ibrahim

2016

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Synthesis of Some Novel Heteroannulated Pyrano[3,2‐c]quinoline‐2,5(6H)‐diones

Hassanin

Abdelkader

2018

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6‐Butyl‐3‐((dimethylamino)methylene)pyrano[3,2‐c]quinolinone and 6‐butyl pyrano[3,2‐c]quinolone‐3‐carbonitrile were efficiently synthesized in good yield. These two new precursors were used to obtain some novel heteroannulated pyrano[3,2‐c]quinolone derivatives from heterocyclization reactions with various binucleophiles. These heteroannulation reactions afforded novel heterocyclic systems fused to the pyranoquinolinone at face c, such as pyrazole, pyrimidine, pyridine, and pyrazolopyranone.

Synthesis and Chemical Reactivity of the Novel 4‐Hydroxy‐6‐methyl‐2,5‐dioxo‐5,6‐dihydro‐2H‐pyrano[3,2‐c]quinoline‐3‐carboxaldehyde

Ibrahim

Hassanin

Gabr

et al. 2018

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in Wiley Online Library (wileyonlinelibrary.com).Vilsmeier-Haack formylation of 3-(4-hydroxy-1-methy1-2-oxo-(1H)-quinolin-3-yl)-3-oxopropanoic acid (2) produced the novel 4-hydroxy-6-methyl-2,5-dioxo-5,6-dihydro-2H-pyrano[3,2-c]quinoline-3carboxaldehyde (4). The chemical reactivity of carboxaldehyde 4 with a diversity of nitrogen nucleophilic reagents was studied, and a variety of products were obtained. Some 1,3,4-oxadiazolyl/1,3,4-thiadiazolyl/ benzothiazolyl linked pyrano[3,2-c]quinoline-2,5(6H)-dione were efficiently synthesized. Structures of the new synthesized products were deduced on the basis of their analytical and spectral data.