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

Active Publication Date: 2019-12-20
NINGBO UNIV
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AI Technical Summary

Problems solved by technology

[0004] The cyclization reactions of enyne derivatives and sulfonyl hydrazides reported in the past are usually accompanied by the introduction of other free radical sources at the same time as the introduction of sulfonyl groups, which cannot meet the needs of organic synthesis diversity and selectivity

Method used

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  • Free radical cyclization reaction method for 1,6-eneyne compounds and sulfonyl hydrazide compounds
  • Free radical cyclization reaction method for 1,6-eneyne compounds and sulfonyl hydrazide compounds
  • Free radical cyclization reaction method for 1,6-eneyne compounds and sulfonyl hydrazide compounds

Examples

Experimental program
Comparison scheme
Effect test

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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Abstract

The invention relates to a high-regioselectivity free radical cyclization reaction method for 1,6-eneyne compounds and sulfonyl hydrazide compounds under mild conditions. The method comprises the following steps: adding one 1,6-eneyne compound, one sulfonyl hydrazide compound, a catalyst, an oxidant and a solvent into a Schlenk reaction flask, and performing a reaction under stirring under a certain temperature and air atmosphere condition to obtain one corresponding sulfone-containing cyclization product.

Description

technical field [0001] The application belongs to the field of organic synthesis, and in particular relates to a high regioselective free radical cyclization reaction method of 1,6-enyne compounds and sulfonyl hydrazide compounds under mild conditions. Background technique [0002] The research on the free radical tandem cyclization reaction of unsaturated hydrocarbons has attracted much attention. It can not only quickly introduce one or more functional groups, but also has a wide range of functional group adaptability, and the electronic effect does not significantly affect it. An efficient way is provided. However, achieving high regioselectivity for such reactions is challenging due to the high reactivity of radical intermediates. Therefore, it is of great scientific significance to develop highly regioselective radical tandem cyclization reactions of unsaturated hydrocarbons. [0003] Sulfone-containing compounds are widely found in pharmaceuticals, natural products a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/38C07D409/12C07B37/10
CPCC07D207/38C07D409/12C07B37/10
Inventor 魏文廷曹婷婷张君尧宋思哲
Owner NINGBO UNIV
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