A Synthesis of 1H-Indazoles via a Cu(OAc)(2)-Catalyzed N-N Bond Formation

A facile synthesis of 1H-indazoles featuring a Cu(OAc)(2)-catalyzed N-N bond formation using oxygen as the terminal oxidant is described. The reaction of readily available 2-aminobenzonitriles with various organometallic reagents led to o-aminoaryl N-H ketimine species. The subsequent Cu(OAc)(2)-cat...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 7; pp. 1690 - 1693
Main Authors Chen, Cheng-yi, Tang, Guangrong, He, Fengxian, Wang, Zhaobin, Jing, Hailin, Faessler, Roger
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 01.04.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
H AMIDATION
SEEDS
FUNCTIONALIZATION
IN-VITRO
ONE-POT SYNTHESIS
INDAZOLE-TYPE ALKALOIDS
EFFICIENT SYNTHESIS
NIGELLA-SATIVA
BENZYDAMINE
DERIVATIVES
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Summary:A facile synthesis of 1H-indazoles featuring a Cu(OAc)(2)-catalyzed N-N bond formation using oxygen as the terminal oxidant is described. The reaction of readily available 2-aminobenzonitriles with various organometallic reagents led to o-aminoaryl N-H ketimine species. The subsequent Cu(OAc)(2)-catalyzed N-N bond formation in DMSO under oxygen afforded a wide variety of 1H-indazoles in good to excellent yields.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00611