α-Diazoacetamides in Sc(OTf)3-Catalyzed Tiffeneau-Demjanov Ring Expansion: Application towards the Synthesis of Rare Bicyclic Pyrazoles

被引：2
|
作者：
Chuprun, Sergey [1 ,2 ]
Dar'in, Dmitry [1 ]
Kantin, Grigory [1 ]
Zhmurov, Petr [1 ]
Krasavin, Mikhail [1 ]
机构：
[1] St Petersburg State Univ, St Petersburg 199034, Russia
[2] Florida Int Univ, Dept Chem & Biochem, 11200 SW 8th St, Miami, FL 33199 USA
来源：
SYNLETT | 2020年 / 31卷 / 04期
基金：
俄罗斯科学基金会;
关键词：
alpha-diazoacetamides; Tiffeneau-Demjanov ring expansion; scandium triflate; beta-keto carboxamides; Lawesson's reagent; bicyclic pyrazoles; COPPER-MEDIATED CONSTRUCTION; C-H; BIS-OXINDOLES; EFFICIENT; KETONES; ACCESS; CYCLOALKANONES; HOMOLOGATION; ENTRY;
D O I：
10.1055/s-0039-1690047
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel Sc(OTf)(3)-catalyzed Tiffeneau-Demjanov ring expansion of six-membered cyclic ketones has been developed. The resulting seven-membered cyclic beta-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.
引用
收藏
页码：373 / 377
页数：5
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