Intramolecular [4+2] cycloaddition of α,β-unsaturated hydrazones as a route to annelated pyridines
✍ Scribed by Roland E. Dolle; W.Paul Armstrong; Antony N. Shaw; Riccardo Novelli
- Book ID
- 104217786
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- French
- Weight
- 205 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
SS:
The first examples of the intramolecular Diels-Alder reaction of a.&unsaturated hydrazones are described. A novel phosphonate (4) has been utilized in the preparation of substrates (2).
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## Abstract 2,2‐Dialkoxy‐3,4‐dihydropyrans (3) can be obtained under mild conditions and in good yields from ketene acetals (1) and α,β‐unsaturated carbonyl compounds (**2**) in the presence of ZnCl~2~. At low temperatures (< −20°C) the reaction between **1** and **2** proceeds as a (2 + 2)‐cycload