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

doi:10.1016/j.tetlet.2009.12.010

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

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

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, 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.

Original language	English
Pages (from-to)	903-906
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	6
DOIs	https://doi.org/10.1016/j.tetlet.2009.12.010
Publication status	Published - Feb 10 2010

Keywords

Cyanovinyl ether
Cycloalkeno[1,2-d]furo[2,3-b]pyridine
Estervinyl ether
Heterocycle
Michael addition
Truce-Smiles rearrangement

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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. / Okuda, Kensuke; Watanabe, Norimasa; Hirota, Takashi et al.
In: Tetrahedron Letters, Vol. 51, No. 6, 10.02.2010, p. 903-906.

Research output: Contribution to journal › Article › peer-review

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title = "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",

abstract = "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, 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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author = "Kensuke Okuda and Norimasa Watanabe and Takashi Hirota and Kenji Sasaki",

year = "2010",

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T1 - Polycyclic N-heterocyclic compounds. Part 61

T2 - A novel Truce-Smiles type rearrangement reaction of 4-(2-cyanovinyloxy)butanenitriles to give cycloalkeno[1,2-d]furo[2,3-b]pyridines

AU - Okuda, Kensuke

AU - Watanabe, Norimasa

AU - Hirota, Takashi

AU - Sasaki, Kenji

PY - 2010/2/10

Y1 - 2010/2/10

N2 - 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, 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.

AB - 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, 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.

KW - Cyanovinyl ether

KW - Cycloalkeno[1,2-d]furo[2,3-b]pyridine

KW - Estervinyl ether

KW - Heterocycle

KW - Michael addition

KW - Truce-Smiles rearrangement

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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

Abstract

Keywords

ASJC Scopus subject areas

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