N-substituted-2-bezilidene-3,4-dihydrobenzo [1,4] oxazine compounds and preparation thereof
A dihydrobenzene and benzylidene technology, applied in the field of organic compounds and synthesis, can solve the problems of low total yield and cumbersome treatment, achieve high conversion rate, optimize the synthesis process, and simplify the post-treatment process
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Embodiment 1
[0022] Example 1: (cis)-2-benzylidene-4-methyl-3,4-dihydrobenzo[1,4]oxazine Synthesis
[0023] 2-(4-methylbenzenesulfonate) phenylmethylamine, phenylacetylene, Paraformaldehyde, dioxane, CuCl, triethylamine, the amount of raw materials is 1.0mmol of 2-(4-methylbenzenesulfonate group) phenylmethylamine, 1.5mmol of phenylacetylene, and 2.0mmol of paraformaldehyde mmol, 3 ml of dioxane, 0.1 mmol of CuCl, and 3.0 mmol of triethylamine were reacted at 110° C. for 20 hours, then potassium hydroxide (10 mmol), 7 ml of ethanol, and 1 ml of water were added, and reacted at 80° C. for 12 hours. 2-(4-Methylbenzenesulfonate group) phenylmethylamine: phenylacetylene: paraformaldehyde: CuCl: triethylamine is 1: 1.5: 2: 0.1: 3, and (cis)-2- Benzylidene-4-methyl-3,4-dihydrobenzo[1,4]oxazine, yield 34%.
[0024] 1 H NMR (CDCl 3 , Me 4 Si) δ 2.76(s, 3H), 3.55(s, 2H), 5.34(s, 1H), 6.64-7.26(m, 7H), 7.60(d, J=8Hz, 2H); 13 C NMR (CDCl 3 , Me 4 Si)δ 38.11, 52.41, 104.55, 112.89, 115.73, 1...
Embodiment 2
[0025] Example 2: (cis)-2-benzylidene-4-methyl-3,4-dihydrobenzo[1,4]oxazine Synthesis
[0026] 2-(4-methylbenzenesulfonate) phenylmethylamine, phenylacetylene, Paraformaldehyde, dioxane, CuCl, triethylamine, the amount of raw materials is 1.0mmol of 2-(4-methylbenzenesulfonate group) phenylmethylamine, 1.5mmol of phenylacetylene, and 2.0mmol of paraformaldehyde mmol, 3ml of dioxane, 0.15mmol of CuCl, 3.0mmol of triethylamine, reacted at 110°C for 20 hours, then added potassium hydroxide (10mmol), 7ml of ethanol, and 1ml of water, and reacted at 80°C for 12 hours, 2-(4-methylbenzenesulfonate group) phenylmethylamine: phenylacetylene: paraformaldehyde: CuCl: triethylamine is 1: 1.5: 2: 0.15: 3, and (cis)-2- Benzylidene-4-methyl-3,4-dihydrobenzo[1,4]oxazine, the yield is 60%.
Embodiment 3
[0027] Example 3: (cis)-2-benzylidene-4-methyl-3,4-dihydrobenzo[1,4]oxazine Synthesis
[0028] 2-(4-methylbenzenesulfonate) phenylmethylamine, phenylacetylene, Paraformaldehyde, dioxane, CuCl, triethylamine, the amount of raw materials is 1.0mmol of 2-(4-methylbenzenesulfonate group) phenylmethylamine, 1.5mmol of phenylacetylene, and 2.0mmol of paraformaldehyde mmol, 3ml of dioxane, 0.2mmol of CuCl, 3.0mmol of triethylamine, reacted at 110°C for 20 hours, then added potassium hydroxide (10mmol), 7ml of ethanol, and 1ml of water, and reacted at 80°C for 12 hours, 2-(4-Methylbenzenesulfonate) phenylmethylamine: phenylacetylene: paraformaldehyde: CuCl: triethylamine is 1: 1.5: 2: 0.2: 3, to get (cis)-2- Benzylidene-4-methyl-3,4-dihydrobenzo[1,4]oxazine, the yield is 85%.
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