An organic molecule modulated chemoselective cyclization of alkynyl nitriles tethered to 2-alkyl substituted chromones with multireactive sites

Liping Huang; Yang Liu; Fuchun Xie; Youhong Hu

doi:10.1021/ol302964x

An organic molecule modulated chemoselective cyclization of alkynyl nitriles tethered to 2-alkyl substituted chromones with multireactive sites

Org Lett. 2012 Dec 21;14(24):6122-5. doi: 10.1021/ol302964x. Epub 2012 Dec 4.

Authors

Liping Huang¹, Yang Liu, Fuchun Xie, Youhong Hu

Affiliation

¹ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 ZuChongZhi Road, China.

PMID: 23210678
DOI: 10.1021/ol302964x

Abstract

A small organic molecule phenylacetonitrile promoted chemoselective cyclization of (chromen-3-yl)alkynylnitriles to generate a novel tetracyclic or tricyclic chromone scaffold has been discovered. Importantly, the phenylacetonitrile serves as an anion transfer reagent changing the normal reaction of the substrate.

Publication types

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

MeSH terms

Acetonitriles / chemistry*
Alkynes / chemistry*
Chromones / chemical synthesis*
Chromones / chemistry
Combinatorial Chemistry Techniques
Cyclization
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
Heterocyclic Compounds, 4 or More Rings / chemistry
Molecular Structure
Nitriles / chemistry*
Stereoisomerism

Substances

Acetonitriles
Alkynes
Chromones
Heterocyclic Compounds, 4 or More Rings
Nitriles
benzyl cyanide