Citation: Liu Bin, Tong Hongjuan, Zhu Zhoujing, Zhang Yanmin, Guo Hui. Synthesis of 3-Secondary Amine Substituted Oxetane-3-Carbonitrile Derivatives[J]. Chemistry, ;2020, 83(10): 946-950. shu

Synthesis of 3-Secondary Amine Substituted Oxetane-3-Carbonitrile Derivatives

Liu Bin ^1,2,, ,
Tong Hongjuan ¹ ,
Zhu Zhoujing ¹ ,
Zhang Yanmin ² ,
Guo Hui ³

1.
School of Pharmacy, Shaanxi Institute of International Trade&Commerce, Xi'an, 712046
2.
Collaborative innovation center of green manufacturing technology for traditional Chinese medicine in Shaanxi province, Xi'an, 712046
3.
College of Pharmacy, Shaanxi University of Chinese Medicine, Xi'an, 712046

Corresponding author: Liu Bin, lb125lb@163.com
Received Date: 7 April 2020
Accepted Date: 26 April 2020

Figures(4)

3-Secondary amine substituted oxetane-3-carbonitrile derivatives (1a~1d) were synthesized by the reaction of secondary amines with oxetan-3-one and trimethylsilyl cyanide in absolute methanol without catalyst. Their structure was confirmed by ¹H NMR, ¹³C NMR and ESI-MS. The effect of conditions on the yield of product 1a was investigated as model reaction. The optimal conditions on the reaction were as follows: the mole ratio of n (isoindoline):n (oxetan-3-one):n (trimethylsilyl cyanide)=2.0:1:2.5, absolute methanol as solvent, the reaction was at 65℃ for 6h. The product of 1a was obtained in 78.3% yield. The application of the target compound was also investigated. 2-(3-Phenyloxetan-3-yl)isoindoline and (3-(isoindolin-2-yl)oxetan-3-yl)(phenyl)methanone were obtained in a yield of 40.1% and 31.5% by the reaction of 1a and phenylmagnesium bromide in tetrahydrofuran at room temperature for 5h.
- Oxetane,
- Derivative,
- Three-component reaction,
- Synthesis
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沈阳化工大学材料科学与工程学院沈阳 110142