New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton

Date

2013-01-01

Author

Dengiz, Çağatay

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We hereby report a new method for preparation of 3,4-dihydroquinolin-2(2H)-one starting from the methyl 2-(2-carboxyethyl)benzoic acid. The acid functionality, adjacent to the methylene, was regiospecifically converted to the desired methyl ester and the remaining acid functionality was transferred into acyl azide. Curtius rearrangement of acyl azide followed by trapping with aniline and alcohols provided the corresponding urea and urethane derivatives. Hydrolysis of methyl ester groups gave the acids. Ring closure in the presence of thionyl chloride resulted in the formation of the 3,4-dihydroquinolin-2(2H)-one skeleton.

Subject Keywords

Quinolinone, Dihydroquinolinone, Acyl azide, Curtius rearrangement

URI

https://hdl.handle.net/11511/37509

Journal

TURKISH JOURNAL OF CHEMISTRY

DOI

https://doi.org/10.3906/kim-1207-35

Collections

Department of Chemistry, Article

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Citation Formats

Ç. Dengiz, “New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton,” TURKISH JOURNAL OF CHEMISTRY, pp. 220–227, 2013, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/37509.