Syntheses of 1-Aryl-5-nitro-1H-indazoles and a General One-Pot Route to 1-Aryl-1H-indazoles

被引：8

作者：

Annor-Gyamfi, Joel K. ^{[1
]}

Gnanasekaran, Krishna Kumar ^{[1
]}

Bunce, Richard A. ^{[1
]}

机构：

[1] Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA

来源：

MOLECULES | 2018年 / 23卷 / 03期

关键词：

1-aryl-5-nitro-1H-indazole; 1-aryl-1H-indazole; arylhydrazone; SNAr reaction; Ullmann reaction; N-ACYLATION-SNAR; CATALYZED INTRAMOLECULAR AMINATION; EFFICIENT SYNTHESIS; SUBSTITUTED; 1H-INDAZOLES; INDAZOLES; DERIVATIVES; HYDRAZONES; CHEMISTRY; PATHWAY;

D O I：

10.3390/molecules23030674

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

An efficient route to substituted 1-aryl-1H-indazoles has been developed and optimized. The method involved the preparation of arylhydrazones from acetophenone or benzaldehyde substituted by fluorine at C2 and nitro at C5, followed by deprotonation and nucleophilic aromatic substitution (SNAr) ring closure in 45-90%. Modification of this procedure to a one-pot domino process was successful in the acetophenone series (73-96%), while the benzaldehyde series (63-73%) required a step-wise addition of reagents. A general one-pot protocol for 1-aryl-1H-indazole formation without the limiting substitution patterns required for the SNAr cyclization has also been achieved in 62-78% yields. A selection of 1-aryl-1H-indazoles was prepared in high yield by a procedure that requires only a single laboratory operation.

引用

页数：13

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