New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton
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.
New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton
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.
Keywords:
Quinolinone, dihydroquinolinone acyl azide, Curtius rearrangement,
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| Bibtex | @ { tbtkchem142003, journal = {Turkish Journal of Chemistry}, issn = {1300-0527}, eissn = {1303-6130}, address = {}, publisher = {TÜBİTAK}, year = {2013}, volume = {37}, pages = {220 - 227}, doi = {10.3906/kim-1207-35}, title = {New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton}, key = {cite}, author = {Dengiz, Çağatay and Balcı, Metin} } |
| APA | Dengiz, Ç , Balcı, M . (2013). New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton . Turkish Journal of Chemistry , 37 (2) , 220-227 . DOI: 10.3906/kim-1207-35 |
| MLA | Dengiz, Ç , Balcı, M . "New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton" . Turkish Journal of Chemistry 37 (2013 ): 220-227 < |
| Chicago | Dengiz, Ç , Balcı, M . "New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton". Turkish Journal of Chemistry 37 (2013 ): 220-227 |
| RIS | TY - JOUR T1 - New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton AU - Çağatay Dengiz , Metin Balcı Y1 - 2013 PY - 2013 N1 - doi: 10.3906/kim-1207-35 DO - 10.3906/kim-1207-35 T2 - Turkish Journal of Chemistry JF - Journal JO - JOR SP - 220 EP - 227 VL - 37 IS - 2 SN - 1300-0527-1303-6130 M3 - doi: 10.3906/kim-1207-35 UR - Y2 - 2021 ER - |
| EndNote | %0 Turkish Journal of Chemistry New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton %A Çağatay Dengiz , Metin Balcı %T New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton %D 2013 %J Turkish Journal of Chemistry %P 1300-0527-1303-6130 %V 37 %N 2 %R doi: 10.3906/kim-1207-35 %U 10.3906/kim-1207-35 |
| ISNAD | Dengiz, Çağatay , Balcı, Metin . "New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton". Turkish Journal of Chemistry 37 / 2 (Şubat 2013): 220-227 . |
| AMA | Dengiz Ç , Balcı M . New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton. Turk J Chem. 2013; 37(2): 220-227. |
| Vancouver | Dengiz Ç , Balcı M . New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton. Turkish Journal of Chemistry. 2013; 37(2): 220-227. |
| IEEE | Ç. Dengiz ve M. Balcı , "New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton", Turkish Journal of Chemistry, c. 37, sayı. 2, ss. 220-227, Şub. 2013, doi:10.3906/kim-1207-35 |
- ISSN: 1300-0527
- Yayın Aralığı: Yılda 6 Sayı
- Yayıncı: TÜBİTAK
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