Free radical cyclization reaction method for 1,6-eneyne compounds and sulfonyl hydrazide compounds
A compound, sulfonyl hydrazide technology, applied in the field of high regioselective free radical cyclization reaction, can solve the problems that cannot meet the needs of organic synthesis diversity and selectivity, and achieve the effect of mild reaction conditions and a wide range of applications
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Examples
Embodiment 1
[0028]
[0029] In the Schlenk bottle, add 1,6-enyne compound (39.8 mg, 0.2 mmol) shown in formula 1a, sulfonyl hydrazide compound (82.4 mg, 0.4 mmol) shown in formula 2a, tert-butyl alcohol peroxide (TBHP , 36.0mg, 0.4mmol), acetonitrile (2mL), then the reactor was stirred and reacted in an air atmosphere at 60°C, and the reaction process was monitored by TLC until the raw material disappeared (reaction time was 12 hours). After the reaction was completed, the reaction The liquid was concentrated under reduced pressure to remove the solvent, and the residue was separated by column chromatography (elution solvent: ethyl acetate / n-hexane) to obtain the target product I-1 (8% yield); 1 H NMR (500MHz, CDCl 3 )δ: 7.77(d, J=8.5Hz, 2H), 7.65(d, J=8.5Hz, 2H), 7.42-7.38(m, 4H), 7.19(t, J=7.5Hz, 1H), 5.40( s, 1H), 5.33(s, 1H), 4.65(d, J=14.0Hz, 1H), 4.49(d, J=14.0Hz, 1H), 3.86(d, J=14.5Hz, 1H), 3.50( d, J=14.5Hz, 1H), 1.37(s, 3H); 13C NMR (125MHz, CDCl 3 )δ: 173.9, 142.1, 140.3,...
Embodiment 2
[0031] The catalyst cuprous iodide (CuI, 3.8mg, 0.02mmol) was added, and the remaining conditions were the same as in Example 1, and the yield of the target product I-1 was 80%.
Embodiment 3
[0033] Catalyst cuprous chloride (CuCl, 2.0mg, 0.02mmol) was added, and the other conditions were the same as in Example 1, and the yield of the target product I-1 was 71%.
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Description
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Application Information
- IPC
- C07D207/38; C07D409/12; C07B37/10
- CPC
- C07D207/38; C07D409/12; C07B37/10
- Inventors
- 魏文廷; 曹婷婷