Three-Component Coupling Reactions of Arynes for the Synthesis of Benzofurans and Coumarins
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, dihydrobenzo...
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| Format: | Article |
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MDPI AG
2014-01-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/19/1/863 |
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| author | Eito Yoshioka Shigeru Kohtani Hideto Miyabe |
| author_facet | Eito Yoshioka Shigeru Kohtani Hideto Miyabe |
| author_sort | Eito Yoshioka |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-19T03:13:22Z |
| format | Article |
| id | doaj.art-5f86e8227e1a4af794286080b32f3062 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-19T03:13:22Z |
| publishDate | 2014-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-5f86e8227e1a4af794286080b32f30622022-12-21T20:37:57ZengMDPI AGMolecules1420-30492014-01-0119186388010.3390/molecules19010863molecules19010863Three-Component Coupling Reactions of Arynes for the Synthesis of Benzofurans and CoumarinsEito Yoshioka0Shigeru Kohtani1Hideto Miyabe2School of Pharmacy, Hyogo University of Health Sciences, 1-3-6, Minatojima, Chuo-ku, Kobe 650-8530, JapanSchool of Pharmacy, Hyogo University of Health Sciences, 1-3-6, Minatojima, Chuo-ku, Kobe 650-8530, JapanSchool of Pharmacy, Hyogo University of Health Sciences, 1-3-6, Minatojima, Chuo-ku, Kobe 650-8530, JapanThe 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.http://www.mdpi.com/1420-3049/19/1/863arynesmulti-component reactiondomino reactionheterocyclessynthesis |
| spellingShingle | Eito Yoshioka Shigeru Kohtani Hideto Miyabe Three-Component Coupling Reactions of Arynes for the Synthesis of Benzofurans and Coumarins Molecules arynes multi-component reaction domino reaction heterocycles synthesis |
| title | Three-Component Coupling Reactions of Arynes for the Synthesis of Benzofurans and Coumarins |
| title_full | Three-Component Coupling Reactions of Arynes for the Synthesis of Benzofurans and Coumarins |
| title_fullStr | Three-Component Coupling Reactions of Arynes for the Synthesis of Benzofurans and Coumarins |
| title_full_unstemmed | Three-Component Coupling Reactions of Arynes for the Synthesis of Benzofurans and Coumarins |
| title_short | Three-Component Coupling Reactions of Arynes for the Synthesis of Benzofurans and Coumarins |
| title_sort | three component coupling reactions of arynes for the synthesis of benzofurans and coumarins |
| topic | arynes multi-component reaction domino reaction heterocycles synthesis |
| url | http://www.mdpi.com/1420-3049/19/1/863 |
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