Thermally-induced skeletal rearrangement of (Z)-O-propargylic α,β-unsaturated aldoximes to multisubstituted pyridine oxides

Itaru Nakamura; Dong Zhang; Masahiro Terada

doi:10.1016/j.tetlet.2011.09.107

Thermally-induced skeletal rearrangement of (Z)-O-propargylic α,β-unsaturated aldoximes to multisubstituted pyridine oxides

Itaru Nakamura, Dong Zhang, Masahiro Terada

Tohoku University

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

25 Citations (Scopus)

Abstract

(Z)-Propargylic oxime ethers derived from α,β-unsaturated aldehydes were converted to the corresponding 2,3,6-trisubstituted pyridine oxides in moderate to acceptable yields with high regioselectivity. The reaction proceeds via a tandem thermal [2,3] rearrangement, 4π electrocyclization, and ring expansion.

Original language	English
Pages (from-to)	6470-6472
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2011.09.107
Publication status	Published - 2011 Nov 30

Keywords

Alkyne
Electrocyclization
Oxime
Pyridine
Skeletal rearrangement

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10.1016/j.tetlet.2011.09.107

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title = "Thermally-induced skeletal rearrangement of (Z)-O-propargylic α,β-unsaturated aldoximes to multisubstituted pyridine oxides",

abstract = "(Z)-Propargylic oxime ethers derived from α,β-unsaturated aldehydes were converted to the corresponding 2,3,6-trisubstituted pyridine oxides in moderate to acceptable yields with high regioselectivity. The reaction proceeds via a tandem thermal [2,3] rearrangement, 4π electrocyclization, and ring expansion.",

keywords = "Alkyne, Electrocyclization, Oxime, Pyridine, Skeletal rearrangement",

author = "Itaru Nakamura and Dong Zhang and Masahiro Terada",

note = "Funding Information: This work was financially supported by a Grant-in-Aid for Scientific Research from Japan Society for Promotion in Science (JSPS). ",

year = "2011",

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doi = "10.1016/j.tetlet.2011.09.107",

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T1 - Thermally-induced skeletal rearrangement of (Z)-O-propargylic α,β-unsaturated aldoximes to multisubstituted pyridine oxides

AU - Nakamura, Itaru

AU - Zhang, Dong

AU - Terada, Masahiro

N1 - Funding Information: This work was financially supported by a Grant-in-Aid for Scientific Research from Japan Society for Promotion in Science (JSPS).

PY - 2011/11/30

Y1 - 2011/11/30

N2 - (Z)-Propargylic oxime ethers derived from α,β-unsaturated aldehydes were converted to the corresponding 2,3,6-trisubstituted pyridine oxides in moderate to acceptable yields with high regioselectivity. The reaction proceeds via a tandem thermal [2,3] rearrangement, 4π electrocyclization, and ring expansion.

AB - (Z)-Propargylic oxime ethers derived from α,β-unsaturated aldehydes were converted to the corresponding 2,3,6-trisubstituted pyridine oxides in moderate to acceptable yields with high regioselectivity. The reaction proceeds via a tandem thermal [2,3] rearrangement, 4π electrocyclization, and ring expansion.

KW - Alkyne

KW - Electrocyclization

KW - Oxime

KW - Pyridine

KW - Skeletal rearrangement

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DO - 10.1016/j.tetlet.2011.09.107

M3 - Article

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EP - 6472

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 48

ER -

Thermally-induced skeletal rearrangement of (Z)-O-propargylic α,β-unsaturated aldoximes to multisubstituted pyridine oxides

Abstract

Keywords

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