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 |
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| Authors: | Kensuke Okuda Norimasa Watanabe Kenji Sasaki |
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| Institution: | a Gifu Pharmaceutical University, 5-6-1 Mitahora-higashi, Gifu 502-8585, Japan
b Faculty of Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-naka, Kita-Ku, Okayama 700-8530, Japan |
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| Abstract: | The cycloalkeno1,2-d]furo2,3-b]pyridine skeleton was conveniently synthesized from fused 4-(2-cyanovinyloxy)butanenitriles in one step through sequential intramolecular Michael addition, β-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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| Keywords: | Truce-Smiles rearrangement Michael addition Cyanovinyl ether Estervinyl ether Cycloalkeno[1 2-d]furo[2 3-b]pyridine Heterocycle |
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