Next Article in Journal
Next Article in Special Issue
Previous Article in Journal
Previous Article in Special Issue
Molecules 2014, 19(1), 863-880; doi:10.3390/molecules19010863
Article

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

,  and *
Received: 16 December 2013; in revised form: 7 January 2014 / Accepted: 8 January 2014 / Published: 13 January 2014
(This article belongs to the Special Issue Domino Reactions)
View Full-Text   |   Download PDF [514 KB, uploaded 18 June 2014]   |   Browse Figures
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


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.

AMA Style

Yoshioka E, Kohtani S, Miyabe H. Three-Component Coupling Reactions of Arynes for the Synthesis of Benzofurans and Coumarins. Molecules. 2014; 19(1):863-880.

Chicago/Turabian Style

Yoshioka, Eito; Kohtani, Shigeru; Miyabe, Hideto. 2014. "Three-Component Coupling Reactions of Arynes for the Synthesis of Benzofurans and Coumarins." Molecules 19, no. 1: 863-880.



Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert