A Microwave-Assisted Domino Rearrangement of Propargyl Vinyl Ethers to Multifunctionalized Aromatic Platforms
✍ Scribed by Dr. David Tejedor; Gabriela Méndez-Abt; Leandro Cotos; Dr. Miguel A. Ramirez; Dr. Fernando García-Tellado
- Publisher
- John Wiley and Sons
- Year
- 2011
- Tongue
- English
- Weight
- 214 KB
- Volume
- 17
- Category
- Article
- ISSN
- 0947-6539
No coin nor oath required. For personal study only.
✦ Synopsis
In memory of Professor Rafael Suau
Propargyl vinyl ethers (PVEs) 1 constitute a privileged group of small size, structurally simple, readily available, and densely functionalized scaffolds. [2][3] Efforts from our group, [2] and others, [3] have revealed the synthetic potential of these platforms in accessing important heterocyclic cores.
The key to the chemical reactivity encoded in these structures is the [3,3] propargylic sigmatropic rearrangement shown in Scheme 1. The allenyl compounds 2, thus obtained, are reactive units and well suited to participate in a wide array of chemical transformations. Thus, in the presence of metallic catalysts, they have been selectively transformed into furans, [3a-d] 2H-pyrans, [3e] dihydropyrans, [3f] 1,2-dihydropyridines, [3g] or pyrroles. [3h] Recently, we have described a metal-free, microwave-assisted domino synthesis of substituted 1,2-dihydropyridines [2c] and pyridines, [2d] from PVEs