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Molecules 2014, 19(1), 863-880; doi:10.3390/molecules19010863

Three-Component Coupling Reactions of Arynes for the Synthesis of Benzofurans and Coumarins

School of Pharmacy, Hyogo University of Health Sciences, 1-3-6, Minatojima, Chuo-ku, Kobe 650-8530, Japan
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Received: 16 December 2013 / Revised: 7 January 2014 / Accepted: 8 January 2014 / Published: 13 January 2014
(This article belongs to the Special Issue Domino Reactions)
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Abstract

The domino three-component coupling reaction of arynes with DMF and active methylenes or methines was studied as a highly efficient method for preparing heterocycles. Coumarin derivative 5 was formed when diethyl malonate (2) or α-bromomalonate (3) were used as a C2-unit. In contrast, dihydrobenzofurans 7a and 7b were obtained by using α-chloroenolates generated from α-chloromalonates 4a and 4b and Et2Zn. The benzofuran 15a could be obtained by using ethyl iodoacetate (14) as a C1-unit. The one-pot conversion of dihydrobenzofurans 7a, 7b and 8a into benzofurans 15a and 15b was also studied. The direct synthesis of benzofuran 15b was achieved by using the active methine 18 having ketone and ester groups.
Keywords: arynes; multi-component reaction; domino reaction; heterocycles; synthesis arynes; multi-component reaction; domino reaction; heterocycles; synthesis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Yoshioka, E.; Kohtani, S.; Miyabe, H. Three-Component Coupling Reactions of Arynes for the Synthesis of Benzofurans and Coumarins. Molecules 2014, 19, 863-880.

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