Preparative routes to spiroacetals derived from chroman-4-one (2,3-dihydro-4H-1-benzopyran-4-one)
✍ Scribed by Peter J. Cremins; Roy Hayes; Timothy W. Wallace
- Publisher
- Elsevier Science
- Year
- 1993
- Tongue
- French
- Weight
- 626 KB
- Volume
- 49
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
Methyl 2-(4-hydroxybutyl)-4-oxo-4~-1-benzopyran-3-carboxylate 6 1s transformed mto the sproacetals 13 and 14 (ratio 5 1) vw treatment with mdomethane&otassmm carbonate, the process mvolvmg sequenaal mtramolecular conjugate addmon and enolate alkylafion The 2,3-epoxlde 7 derived from 6 undergoes spuwychsation to the hydroxyesters 16 and 17 upon treatment with acids The siruchues of 13 and 16 were confirmed by X-ray crystallography
📜 SIMILAR VOLUMES
The title compound, also known as intricatinol, C~17~H~14~O~5~, is a homoisoflavanoid that was isolated for the first time from the twigs and stems of __Caesalpinia digyna__ Rottler. The pyran ring is in an envelope form. O—H...O intramolecular hydrogen bonds are observed. Symmetry-related molecules
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## Abstract magnified image The title aldehyde **1** reacts smoothly with the enamine moiety of **2**‐aminochromone **2** to produce hitherto unreported 3‐(2‐hydroxybenzoyl)‐5__H__‐1‐benzopyrano[2,3‐__b__]pyridin‐5‐one (azaxanthone) **5**. This reaction has been extended for the synthesis of bisaz