Synthesis 2020; 52(07): 1035-1046
DOI: 10.1055/s-0039-1690799
paper
© Georg Thieme Verlag Stuttgart · New York

One-Pot Access to 4-Aryl-2-arylacetoxynaphthalenes via Benz­annulation of Oxygenated Arylacetic Acids and Alkyl Aryl Ketones

a   Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan   Email: mychang@kmu.edu.tw
b   Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan
,
Shin-Mei Chen
a   Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan   Email: mychang@kmu.edu.tw
,
Yu-Ting Hsiao
a   Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan   Email: mychang@kmu.edu.tw
› Author Affiliations
The authors would like to thank the Ministry of Science and Technology of the Republic of China for its financial support (MOST 106-2628-M-037-001-MY3).
Further Information

Publication History

Received: 25 November 2019

Accepted after revision: 23 December 2019

Publication Date:
27 January 2020 (online)


Abstract

Trifluoroacetic anhydride mediated one-pot intermolecular formal (4+2) benzannulation of oxygenated arylacetic acids with alkyl aryl ketones provides 4-aryl-2-arylacetoxynaphthalenes in moderate to good yields in the presence of H3PO4 in an open-vessel in a straightforward procedure. A plausible mechanism is proposed and discussed. This protocol provides a highly effective ring-closure via two carbon–carbon (C–C) and one carbon–oxygen (C–O) bond-formation events.

Supporting Information