A convenient and efficient protocol for the synthesis of 4(1H)-cinnolones, 1,4-dihydrocinnolines, and cinnolines in aqueous medium: application for detection of nitrite ions

3-Aryl/alkyl-4(1H)-cinnolones are obtained in one step from 2-aryl/alkylethynyl aniline by reaction with sodium nitrite and dilute hydrochloric acid via Richter cyclization. The alkyl cinnolones on reduction with Sn/HCl furnish 1,4-dihydro-3-alkylcinnolines, which are converted to 3-alkylcinnolines by treatment with NaNO2/HCl/KI. The whole process is carried out in aqueous medium at ambient temperature within a short reaction period. The reaction of 2-phenylethynyl aniline exhibits yellow color with UV absorbance at 391 nm and has been successfully tested for the detection of nitrite ions in water at parts per million concentration.

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