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α-Diazoacetamides in Sc(OTf)3-Catalyzed Tiffeneau–Demjanov Ring Expansion: Application towards the Synthesis of Rare Bicyclic Pyrazoles
Synlett ( IF 1.7 ) Pub Date : 2020-01-09 , DOI: 10.1055/s-0039-1690047
Sergey Chuprun , Dmitry Dar’in , Grigory Kantin , Petr Zhmurov , Mikhail Krasavin 1
Affiliation  

A novel Sc(OTf)3-catalyzed Tiffeneau–Demjanov ring expansion of six-membered cyclic ketones has been developed. The resulting seven-membered cyclic β-keto carboxamides were found to be versatile precursors to rare bicyclic pyrazoles obtained in modest to good yields via condensation with aryl hydrazines in the presence of Lawesson’s reagent.

中文翻译:

α-重氮乙酰胺在 Sc(OTf)3-催化的 Tiffeneau-Demjanov 环扩展中的应用:在稀有双环吡唑的合成中的应用

已经开发了一种新型的 Sc(OTf)3 催化的六元环酮的 Tiffeneau-Demjanov 环扩展。发现所得的七元环状 β-酮甲酰胺是稀有双环吡唑的通用前体,通过在劳森试剂的存在下与芳基肼缩合以中等至良好的产率获得。
更新日期:2020-01-09
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