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Journals / Turkish Journal of Chemistry / 2013 / Cilt: 37 - Sayı: 2

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

Çağatay DENGİZ
Metin BALCI
Pages
220–227
Publication Date
2013-02-01
DOI
—
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Ring closure in the presence of thionyl chloride resulted in the formation of the 3,4-dihydroquinolin-2(2H)-one skeleton.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:We hereby report a new method for preparation of 3,4-dihydroquinolin-2(2H)-one starting from the methyl 2-(2-carboxyethyl)benzoic acid.
📊
Key Findings & Data: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.
💡
Conclusion & Impact:Ring closure in the presence of thionyl chloride resulted in the formation of the 3,4-dihydroquinolin-2(2H)-one skeleton.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Quinolinone · dihydroquinolinone · acyl azide

Abstract

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.

Özet

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.

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Cite This Article

DENGİZ, Ç., BALCI, M. (2013). New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton. Turkish Journal of Chemistry, Cilt: 37 - Sayı: 2, 220–227. https://ajindex.com/articles/184718

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