One-pot synthesis using azo coupling: metal- and protecting-group-free synthesis of 5-hydroxy 2H-indazoles and 6-hydroxy cinnolin-3(2H)-ones

被引：0

作者：

Miyazaki, Yu ^{[1
]}

Itoh, Shotaroh ^{[2
]}

Kondo, Masaru ^{[3
]}

机构：

[1] Ibaraki Univ, Grad Sch Sci & Engn, Dept Mat Sci & Engn, 4-12-1 Naka Narusawa, Hitachi, Ibaraki 3168511, Japan

[2] Ibaraki Univ, Dept Mat Sci & Engn, 4-12-1 Naka Narusawa, Hitachi, Ibaraki 3168511, Japan

[3] Univ Shizuoka, Sch Pharmaceut Sci, 52-1 Yada Suruga Ku, Shizuoka 4228526, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2025年 / 98卷 / 05期

基金：

日本学术振兴会;

关键词：

2H-indazole; azo coupling; one-pot synthesis; CONSECUTIVE CONDENSATION; C-N; 2-ARYL-2H-INDAZOLES; AZOBENZENES; DERIVATIVES; CYCLIZATION; LIGANDS;

D O I：

10.1093/bulcsj/uoaf034

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Azo coupling is a well-known method for the synthesis of azobenzenes; however, a one-pot protocol that uses this reaction has rarely been investigated due to its unique reaction conditions and azobenzene stability. Herein, we report a one-pot azo coupling/SOCl2-mediated intramolecular cyclization protocol that uses 3-hydroxybenzyl alcohols and diazonium salts to afford 5-hydroxy 2H-indazoles in yields of up to 82%. This process does not require transition metal catalysts, harsh conditions, long reaction times, or hydroxy group protection. 6-Hydroxy cinnolin-3(2H)-ones were also prepared using this one-pot system.

引用

页数：7

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