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An Easy Palladium-Catalyzed Access to Substituted 3-Methylene-3,4-dihydro-2H-1,5-benzodioxepines
| Content Provider | Semantic Scholar |
|---|---|
| Author | Damez, Céline Labrosse, Jean-Robert Lhoste, Paul Sinou, Denis |
| Copyright Year | 2001 |
| Abstract | 2H-1,5-Benzodioxepin-3(4H)-one (4a) is a key intermediate in the synthesis of analogs of 3,4-dihydro-2H-1,5benzodioxepine, which possess interesting biological properties. For example, members of this series constitute a unique class of -adrenergic stimulants and have also interesting bronchial dilator activity.1 The antifungal strobilurins I and K are also derivatives of 3,4-dihydro-2H-1,5benzodioxepine.2 These compounds have been obtained in very low yields by condensation of benzene-1,2-diol (1a) and 1,3-dichloro-2-hydroxypropane followed by oxidation with KMnO4 3 or by an allylation-epoxidation-cyclization-oxidation sequence.2 An alternative synthesis started with the condensation of benzene-1,2-diol (1a) with ethyl bromoacetate. Dieckmann cyclization of the obtained diester with sodium tert-butoxide yielded 2H1,5-benzodioxepin-3(4H)-one (4a).4 In another case, 6methoxy-3-oxo-2H-[1,5]-benzodioxepine was obtained by Thorpe cyclization of 1,2-bis(cyanomethoxy)benzene, affording an enaminonitrile which was easily hydrolyzed to the ketone 4a.1 |
| Starting Page | 1456 |
| Ending Page | 1458 |
| Page Count | 3 |
| File Format | PDF HTM / HTML |
| DOI | 10.1002/chin.200146159 |
| Volume Number | 32 |
| Alternate Webpage(s) | http://www.xiuzhengrd.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-16092.pdf |
| Alternate Webpage(s) | https://doi.org/10.1002/chin.200146159 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
