Base-Mediated Cyclization Reaction of 2-(5-Hydroxy-1-pentynyl)benzonitriles to 4-Amino-2,3-dihydronaphtho[2,3-b]furanes and Synthesis of Furanonaphthoquinones

Chih-Jyun Tsai; Chin-Chau Chen; Chih-Wei Tsai; Ming-Jung Wu

doi:10.1021/acs.joc.5b02514

Base-Mediated Cyclization Reaction of 2-(5-Hydroxy-1-pentynyl)benzonitriles to 4-Amino-2,3-dihydronaphtho[2,3-b]furanes and Synthesis of Furanonaphthoquinones

J Org Chem. 2016 May 6;81(9):3882-9. doi: 10.1021/acs.joc.5b02514. Epub 2016 Apr 11.

Authors

Chih-Jyun Tsai¹, Chin-Chau Chen¹, Chih-Wei Tsai², Ming-Jung Wu^{1

2}

Affiliations

¹ Department of Chemistry, National Sun Yat-sen University , Kaohsiung, Taiwan 804.
² Department of Medicinal and Applied Chemistry, Kaohsiung Medical University , Kaohsiung, Taiwan 807.

PMID: 27045218
DOI: 10.1021/acs.joc.5b02514

Abstract

An efficient transformation of 2-(5-hydroxy-1-pentynyl)benzonitriles 5 to furanonaphthoquinones 11 is presented. Treatment of 5 with 1.5 equiv of NaOMe in DMSO at 140 °C for 0.5 h gave 6 in good yields. Conversion of 6 to 11 was carried out by oxidation of 6 with Fremy's salt and KH2PO4 in acetone and water, followed by dehydrogenation using palladium on charcoal in diphenylether at reflux temperature.

Publication types

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