Citation: Qian ZHANG, Ying CHEN, Yun Hong ZHENG, Wan Yun SHENG, Peng XIA, Yi XIA, Zheng Yu YANG, Kuo Hsiung LEE. The Synthesis of 7-[1-Aza-2-(dimethylamino)vinyl]-4-methylhydroquinolin-2-ones and their Isomerism in Different Solvents[J]. Chinese Chemical Letters, ;2001, 12(1): 11-14. shu

The Synthesis of 7-[1-Aza-2-(dimethylamino)vinyl]-4-methylhydroquinolin-2-ones and their Isomerism in Different Solvents

1.
Department of Organic Chemistry The School of Pharmacy Shanghai Medical University 138 Yi Xue Yuan Road Shanghai 200032;
2.
Natural Products Laboratory School of Pharmacy University of North Carolina Chapel Hill NC 27599 USA

Received Date: 12 June 2000

The reaction of 7-amino-4-methyl-2(1H)-quinolone 1 and its 6-methyl derivative 2 with Vilsmeier reagent (DMF and POCl₃) afforded 7-[1-aza-2-(dimethylamino)vinyl]-4-methyl-hydro-quinolin-2-one 3 and 7-[1-aza-2-(dimethylamino)vinyl]-4,6-dimethylhydroquinolin-2-one 4, respec-tively. ¹H-NMR analysis in different solvents indicated that isomerism occurred due to hindered rotation around the (CH₃)₂N-C:N σ-bond. The rotational energy barrier of 3 was calculated.
- 7-[1-Aza-2-(dimethylamino)vinyl]-hydroquinolin-2-ones,
- isomerism,
- ¹H-NMR.
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