Parallel Synthesis of Pyrazolone-Fused Cinnolines by the Palladium-Catalyzed [4+2] Annulation of Pyrazol-3-ones with Substituted Allenoates

被引：0

作者：

Chiu, Wei-Jung ^{[1
]}

Chu, Ting-Yen ^{[1
]}

Barve, Indrajeet J. ^{[3
]}

Sun, Chung-Ming ^{[1
,2
]}

机构：

[1] Natl Yang Ming Chiao Tung Univ, Dept Appl Chem, Hsinchu 30010, Taiwan

[2] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 80708, Taiwan

[3] MES Abasaheb Garware Coll, Dept Chem, Pune 411004, Maharashtra, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 89卷 / 01期

关键词：

C-H ACTIVATION; DECARBOXYLATIVE ORTHO-ACYLATION; N-NITROSOANILINES; SPIROPYRAZOLONES; DERIVATIVES;

D O I：

10.1021/acs.joc.3c02165

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of pyrazolone-fused cinnolines from pyrazol-3-ones and alpha,gamma-substituted allenoates via a palladium-catalyzed C-H activation/annulation cascade was developed. Mechanistic studies revealed the course of the reaction. Initially, N-acyl-valine ligand-assisted ortho-C-H activation gives ortho-alkenylated intermediate. Subsequent cyclopalladation and migratory insertion of allenoate give a seven-membered palladacycle. Reductive elimination finally furnishes pyrazolone-fused cinnolines.

引用

页码：395 / 401

页数：7

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