Efficient synthesis of maleimides and carbazoles via Zn(OTf)(2)-catalyzed tandem annulations of isonitriles and allenic esters

Yuanzhen Li; Haixia Zou; Jianxian Gong; Jing Xiang; Tuoping Luo; Junmin Quan; Guoxin Wang; Zhen Yang

doi:10.1021/ol7018086

Efficient synthesis of maleimides and carbazoles via Zn(OTf)(2)-catalyzed tandem annulations of isonitriles and allenic esters

Org Lett. 2007 Sep 27;9(20):4057-60. doi: 10.1021/ol7018086. Epub 2007 Aug 29.

Authors

Yuanzhen Li¹, Haixia Zou, Jianxian Gong, Jing Xiang, Tuoping Luo, Junmin Quan, Guoxin Wang, Zhen Yang

Affiliation

¹ Laboratory of Chemical Genomics, Shenzhen Graduate School, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Peking University, Beijing 100871, China.

PMID: 17725362
DOI: 10.1021/ol7018086

Abstract

Lewis acid Zn(OTf)(2)-catalyzed tandem annulations of isonitriles and allenic esters which lead to efficient and flexible syntheses of a range of biologically significant maleimides and carbazoles and related compounds are reported. A mechanistic rationale is proposed to account for the observed reactivity.

Publication types

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

MeSH terms

Carbazoles / chemical synthesis*
Carbazoles / chemistry
Carbazoles / pharmacology
Catalysis
Enzyme Inhibitors / chemical synthesis
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / pharmacology
Esters / chemistry*
Maleimides / chemical synthesis*
Maleimides / chemistry
Maleimides / pharmacology
Models, Molecular
Molecular Structure
Nitriles / chemistry*
Phosphotransferases / antagonists & inhibitors
Phosphotransferases / metabolism
Poly(ADP-ribose) Polymerase Inhibitors
Poly(ADP-ribose) Polymerases / metabolism
Zinc Compounds / chemistry*

Substances

Carbazoles
Enzyme Inhibitors
Esters
Maleimides
Nitriles
Poly(ADP-ribose) Polymerase Inhibitors
Zinc Compounds
Poly(ADP-ribose) Polymerases
Phosphotransferases