Efficient synthesis of 5,6-dihydroxyindole dimers, key eumelanin building blocks, by a unified o-ethynylaniline-based strategy for the construction of 2-linked biindolyl scaffolds

Luigia Capelli; Paola Manini; Alessandro Pezzella; Alessandra Napolitano; Marco d'Ischia

doi:10.1021/jo901259s

Efficient synthesis of 5,6-dihydroxyindole dimers, key eumelanin building blocks, by a unified o-ethynylaniline-based strategy for the construction of 2-linked biindolyl scaffolds

J Org Chem. 2009 Sep 18;74(18):7191-4. doi: 10.1021/jo901259s.

Authors

Luigia Capelli¹, Paola Manini, Alessandro Pezzella, Alessandra Napolitano, Marco d'Ischia

Affiliation

¹ Department of Organic Chemistry and Biochemistry, University of Naples Federico II, Complesso Universitario Monte S. Angelo, via Cintia 4, I-80126 Naples, Italy.

PMID: 19663515
DOI: 10.1021/jo901259s

Abstract

A unified convenient strategy for the synthesis of 5,6-dihydroxyindole-derived 2,7'-, 2,2'-, and 2,3'-biindolyls is reported, which is based on proper manipulation of key o-ethynylaniline precursors. By the same methodology 5,6-diacetoxy-7-iodoindole can also be obtained in good yield.

Publication types

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

MeSH terms

Acetylene / analogs & derivatives*
Acetylene / chemistry
Aniline Compounds / chemistry*
Cyclization
Dimerization
Enzyme Inhibitors / chemical synthesis*
Indoles / chemical synthesis
Indoles / chemistry*
Melanins / chemistry*
Models, Chemical
Oxidation-Reduction

Substances

2-ethynylaniline
5,6-diacetoxy-7-iodoindole
Aniline Compounds
Enzyme Inhibitors
Indoles
Melanins
eumelanin
Acetylene
5,6-dihydroxyindole