Copper(I)-catalyzed synthesis of 5-arylindazolo[3,2-b]quinazolin-7(5H)-one via Ullmann-type reaction

Dong-Sheng Chen; Guo-Lan Dou; Yu-Ling Li; Yun Liu; Xiang-Shan Wang

doi:10.1021/jo400420b

Copper(I)-catalyzed synthesis of 5-arylindazolo[3,2-b]quinazolin-7(5H)-one via Ullmann-type reaction

J Org Chem. 2013 Jun 7;78(11):5700-4. doi: 10.1021/jo400420b. Epub 2013 May 23.

Authors

Dong-Sheng Chen¹, Guo-Lan Dou, Yu-Ling Li, Yun Liu, Xiang-Shan Wang

Affiliation

¹ School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou Jiangsu 221116, PR China.

PMID: 23675901
DOI: 10.1021/jo400420b

Abstract

The treatment of 2-amino-N'-arylbenzohydrazide and o-halogenated benzaldehyde in the presence of CuBr and Cs2CO3 gave 5-arylindazolo[3,2-b]quinazolin-7(5H)-one in high yields. This procedure contains an Ullmann-type reaction and provides an efficient method to construct fused tetracyclic heterocycles.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bromides / chemistry*
Catalysis
Copper / chemistry*
Molecular Structure
Quinazolinones / chemical synthesis*
Quinazolinones / chemistry

Substances

5-phenylindazolo(3,2-b)quinazolin-7(5H)-one
Bromides
Quinazolinones
cupric bromide
Copper