An Efficient Synthesis of 3‐(1 H‐ Tetrazol‐5‐yl)coumarins (=3‐(1 H ‐Tetrazol‐5‐yl)‐2 H ‐1‐benzopyran‐2‐ones) via Domino Knoevenagel Condensation, Pinner Reaction, and 1,3‐Dipolar Cycloaddition in Water
A novel straightforward synthesis of 3‐(1 H ‐tetrazol‐5‐yl)coumarins (=3‐(1 H ‐tetrazol‐5‐yl)‐2 H ‐1‐benzopyran‐2‐ones) 6 via domino Knoevenagel condensation, Pinner reaction, and 1,3‐dipolar cycloaddition of substituted salicylaldehydes (=2‐hydroxybenzaldehydes), malononitrile (propanedinitrile), a...
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Veröffentlicht in: | Helvetica chimica acta 2012-09, Vol.95 (9), p.1600-1604 |
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Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | A novel straightforward synthesis of 3‐(1
H
‐tetrazol‐5‐yl)coumarins (=3‐(1
H
‐tetrazol‐5‐yl)‐2
H
‐1‐benzopyran‐2‐ones)
6
via
domino
Knoevenagel
condensation,
Pinner
reaction, and 1,3‐dipolar cycloaddition of substituted salicylaldehydes (=2‐hydroxybenzaldehydes), malononitrile (propanedinitrile), and sodium azide in H
2
O is reported (
Scheme 1
and
Table 2
). This general protocol provides a wide variety of 3‐(1
H
‐tetrazol‐5‐yl)coumarins in good yields under mild reaction conditions. |
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ISSN: | 0018-019X 1522-2675 |
DOI: | 10.1002/hlca.201200031 |