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Polycyclic N-heterocyclic compounds. Part 61: A novel Truce–Smiles type rearrangement reaction of 4-(2-cyanovinyloxy)butanenitriles to give cycloalkeno[1,2-d]furo[2,3-b]pyridines

✍ Scribed by Kensuke Okuda; Norimasa Watanabe; Takashi Hirota; Kenji Sasaki

Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
266 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

furo[2,3-b]

pyridine Heterocycle a b s t r a c t

The cycloalkeno [1,2-d]furo [2,3-b]pyridine skeleton was conveniently synthesized from fused 4-(2-cyanovinyloxy)butanenitriles in one step through sequential intramolecular Michael addition, b-elimination and intramolecular nucleophilic addition. This sequence thus consists of a novel Truce-Smiles type rearrangement followed by cyclization. The 5-amino derivatives were transformed further to lactams in good yields.

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ChemInform Abstract: Polycyclic N-Hetero
ChemInform Abstract: Polycyclic N-Heterocyclic Compounds. Part 61. A Novel Truce—Smiles Type Rearrangement Reaction of 4-(2-Cyanovinyloxy)butanenitriles to Give Cycloalkeno[1,2-d]furo[2,3-b]pyridines.
✍ Kensuke Okuda; Norimasa Watanabe; Takashi Hirota; Kenji Sasaki 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 29 KB 👁 1 views

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