Tandem Friedel-Crafts Annulation to Novel Perylene Analogues

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2008 Jul 18

PMID 18630879

Citations 3

Authors

Mark A Penick

Mathew P D Mahindaratne

Robert D Gutierrez

Terrill D Smith

Edward R T Tiekink

George R Negrete

Affiliations

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Abstract

Novel dialkyloxy- and dihydroxyoctahydroperylenes are regioselectively available via a new tandem Friedel-Crafts alkylation of tetrahydronaphthalene precursors followed by oxidative aromatization. Heating of 5-alkyloxy-1-tetralol with p-toluenesulfonic acid in sulfolane gave the corresponding octahydroperylenes in moderate yields. Studies with Lewis acids and tetralin-1,5-diol in acetonitrile at room temperature provided the 4,10-dihydroxy analogue cleanly, albeit in reduced yields. Examples of these new series of perylene analogues were partially oxidized to the corresponding contiguously aromatic, anthracene core products or fully aromatized to 3,9-dialkyloxyperylenes in good yields.

Citing Articles

The photophysical Characterisation of Novel 3,9-Dialkyloxy- and Diacyloxyperylenes.

Fuini 3rd J, Surampudi A, Penick M, Mahindaratne M, Negrete G, Brancaleon L Dyes Pigm. 2014; 88(2):204-211.

PMID: 25473140 PMC: 4248675. DOI: 10.1016/j.dyepig.2010.06.009.

Interaction of human serum albumin with novel 3,9-disubstituted perylenes.

Farooqi M, Penick M, Negrete G, Brancaleon L Protein J. 2013; 32(6):493-504.

PMID: 23975144 PMC: 3871871. DOI: 10.1007/s10930-013-9508-z.

4,10-Diall-yloxy-1,2,3,6b,7,8,9,12b-octa-hydro-perylene.

Smith T, Mahindaratne M, Penick M, Negrete G, Daniels L, Tiekink E Acta Crystallogr Sect E Struct Rep Online. 2011; 66(Pt 1):o96.

PMID: 21580191 PMC: 2980038. DOI: 10.1107/S160053680905243X.

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