Synthesis and reactions of some new allyl furobenzopyranone derivatives
✍ Scribed by El-Sayed I. El-Desoky
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2007
- Tongue
- English
- Weight
- 428 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
magnified image
Reaction of visnaginone 1 with allyl bromide gave O‐allyl visnaginone 2 which underwent Claisen rearrangement to yield 7‐allylbenzofuran derivative 3. Reaction of 3 with different aromatic aldehydes gave the corresponding 5‐cinnamoylbenzofuran derivatives 4a‐d. Condensation of the latter chalcones 4a,c,d with hydrazine hydrate and phenylhydrazine provided, the corresponding pyrazoline derivatives 7a‐f. Claisen condensation of compound 3 with ethyl acetate and diethyl carbonate afforded Claisen adducts 8 and 12 which easily cyclized to 9 and 13, which are endowed with interesting biological properties.
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## Abstract magnified image Reaction of visnaginone which derived from the naturally occurring compound “visnagine”, with allyl bromide gave __O__‐allyl visnaginone **1**, which underwent Claisen rearrangement to yield 7‐allylbenzofuran **2** derivative. Vilsmeier Haack formylation of **2** afford