Rh(III)-Catalyzed Direct Coupling of Azobenzenes with α-Diazo Esters: Facile Synthesis of Cinnolin-3(2H)-ones

Satyasheel Sharma; Sang Hoon Han; Sangil Han; Wontae Ji; Jongchan Oh; Seok-Yong Lee; Joa Sub Oh; Young Hoon Jung; In Su Kim

doi:10.1021/acs.orglett.5b01298

Rh(III)-Catalyzed Direct Coupling of Azobenzenes with α-Diazo Esters: Facile Synthesis of Cinnolin-3(2H)-ones

Org Lett. 2015 Jun 5;17(11):2852-5. doi: 10.1021/acs.orglett.5b01298. Epub 2015 May 20.

Authors

Satyasheel Sharma¹, Sang Hoon Han¹, Sangil Han¹, Wontae Ji¹, Jongchan Oh¹, Seok-Yong Lee¹, Joa Sub Oh², Young Hoon Jung¹, In Su Kim¹

Affiliations

¹ †School of Pharmacy, Sungkyunkwan University, Suwon 440-746, Republic of Korea.
² ‡College of Pharmacy, Dankook University, Cheonan 330-714, Republic of Korea.

PMID: 25990571
DOI: 10.1021/acs.orglett.5b01298

Abstract

The rhodium(III)-catalyzed direct C-H functionalization of azobenzenes with α-diazo compounds is described. These transformations provide the facile and efficient construction of C2-alkylated azobenzenes or highly substituted cinnolin-3(2H)-ones. Furthermore, this protocol leads to the formation of cinnolin-3(2H)-ones using a diazo derivative of Meldrum's acid.

Publication types

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

MeSH terms

Azo Compounds / chemistry*
Catalysis
Dioxanes / chemistry*
Esters
Heterocyclic Compounds, 2-Ring / chemical synthesis*
Heterocyclic Compounds, 2-Ring / chemistry
Molecular Structure
Rhodium / chemistry*

Substances

Azo Compounds
Dioxanes
Esters
Heterocyclic Compounds, 2-Ring
Meldrum's acid
Rhodium
azobenzene
cinnoline