Expeditious Synthesis of 2‑Phenylquinazolin-4-amines via a Fe/Cu Relay-Catalyzed Domino Strategy

A highly efficient Fe/Cu relay-catalyzed domino protocol has been developed for the synthesis of 2-phenylquinazolin-4-amines from commercially available ortho-halogenated benzonitriles, aldehydes, and sodium azide. This elegant domino process involved consecutive iron-mediated [3 + 2] cycloaddition,...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 17; no. 17; pp. 4236 - 4239
Main Authors Jia, Feng-Cheng, Zhou, Zhi-Wen, Xu, Cheng, Cai, Qun, Li, Deng-Kui, Wu, An-Xin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.09.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SODIUM-AZIDE
TANDEM REACTIONS
CYCLOADDITION
3-COMPONENT SYNTHESIS
DIRECT AMINATION
ONE-POT SYNTHESIS
ARYL AZIDES
C-H BONDS
CYCLIZATION
QUINAZOLINES
Online AccessGet full text

Cover

More Information
Summary:A highly efficient Fe/Cu relay-catalyzed domino protocol has been developed for the synthesis of 2-phenylquinazolin-4-amines from commercially available ortho-halogenated benzonitriles, aldehydes, and sodium azide. This elegant domino process involved consecutive iron-mediated [3 + 2] cycloaddition, copper-catalyzed SNAr, reduction, cyclization, oxidation, and copper-catalyzed denitrogenation sequences. The formed structure is the privileged core in drugs and bioactive molecules.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02020