Insight into and Computational Studies of the Selective Synthesis of 6H-Dibenzo[b,h]xanthenes

Paula F Carneiro; Maria do Carmo F R Pinto; Roberta K F Marra; Vinícius R Campos; Jackson Antônio L C Resende; Maicon Delarmelina; José Walkimar M Carneiro; Emerson S Lima; Fernando de C da Silva; Vitor F Ferreira

doi:10.1021/acs.joc.6b00864

Insight into and Computational Studies of the Selective Synthesis of 6H-Dibenzo[b,h]xanthenes

J Org Chem. 2016 Jul 1;81(13):5525-37. doi: 10.1021/acs.joc.6b00864. Epub 2016 Jun 17.

Affiliations

¹ Universidade Federal do Rio de Janeiro , Instituto de Pesquisas de Produtos Naturais, 21944-970 Rio de Janeiro, RJ, Brazil.
² Universidade Federal Fluminense , Instituto de Química, 24020-150 Niterói, RJ, Brazil.
³ Universidade Federal do Amazonas , Faculdade de Ciências da Saúde, 69010-300 Manaus, AM, Brazil.

PMID: 27281677
DOI: 10.1021/acs.joc.6b00864

Abstract

Starting from 2-hydroxy-1,4-naphthoquinone (lawsone), we synthesized eight new 6H-dibenzo[b,h]xanthene derivatives selectively under solvent-free conditions. Spectroscopic investigations confirmed that only the isomer 6H-dibenzo[b,h]xanthene was obtained in all eight cases. Computational studies provide a rationalization for the selective appearance of these isomers having as an intermediate an addition product.

Publication types

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