Selective access to dipyrazolo-fused pyridines via formal [3 + 2 + 1] heteroannulation of methyl ketones with pyrazol-5-amines,Organic Chemistry Frontiers

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Selective access to dipyrazolo-fused pyridines via formal [3 + 2 + 1] heteroannulation of methyl ketones with pyrazol-5-amines
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2017-11-14 00:00:00 , DOI: 10.1039/c7qo00941k
Qinghe Gao _{1,

2,

3,

4,

5} , Shuang He _{1,

2,

3,

4} , Xia Wu _{5,

6,

7,

8,

9} , Jingjing Zhang _{5,

6,

7,

8,

9} , Suping Bai _{1,

2,

3,

4} , Yandong Wu _{5,

6,

7,

8,

9} , Anxin Wu _{5,

6,

7,

8,

9}

Affiliation

A fascinating new form of the Hantzsch reaction with methyl ketones and pyrazol-5-amines for the selective synthesis of dipyrazolo-fused pyridines has been discovered. This special [3 + 2 + 1] heteroannulation was accomplished via the domino generation of two C–C bonds and one C–N bond. Preliminary mechanistic studies indicated that the I₂/DMSO system realized the oxidative carbonylation of Csp³–H of methyl ketones, while Cu(OTf)₂ acted as a relay reagent to accelerate this transformation.

中文翻译：

通过吡唑-5-胺与甲基酮进行正式的[3 + 2 + 1]杂环化反应，选择性地获得与吡唑并有吡啶的吡啶

已经发现了一种引人入胜的新形式的Hantzsch反应，可与甲基酮和吡唑-5-胺选择性合成吡唑并与吡啶的吡啶。这种特殊的[3 + 2 + 1]杂环化是通过多米诺骨牌产生两个C–C键和一个C–N键来实现的。初步的机理研究表明，I ₂ / DMSO系统实现了甲基酮Csp ³ -H的氧化羰基化作用，而Cu（OTf）₂充当了中继剂以加速这种转变。

更新日期：2017-11-23

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