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

作者：Dey Raju; Ranu Brindaban C^*

来源：Tetrahedron, 2011, 67(46): 8918-8924.

DOI：10.1016/j.tet.2011.09.016

• Cinnolone
• Dihydrocinnoline
• Cinnoline
• Richter cyclization
• Detection of nitrite ion

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.

• 出版日期2011-11-18