Synthesis of 1,6-dihydropyrimidines via copper-catalyzed multistep cascade reactions between O-propargylic aldoximes and isocyanates

Itaru Nakamura; Toshiki Onuma; Dong Zhang; Masahiro Terada

doi:10.1016/j.tetlet.2013.12.105

Synthesis of 1,6-dihydropyrimidines via copper-catalyzed multistep cascade reactions between O-propargylic aldoximes and isocyanates

Itaru Nakamura, Toshiki Onuma, Dong Zhang, Masahiro Terada

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

16 Citations (Scopus)

Abstract

Multi-step cascade reactions of O-propargylic oximes with isocyanates were carried out in the presence of copper catalysts to afford the corresponding 1,6-dihydropyrimidines in good yields. The multi-step reactions consisted of a 2,3-rearrangement, a [3+2] cycloaddition, decarboxylative ring opening involving a 1,4-hydrogen shift, and a 6π-electrocyclization.

Original language	English
Pages (from-to)	1178-1182
Number of pages	5
Journal	Tetrahedron Letters
Volume	55
Issue number	6
DOIs	https://doi.org/10.1016/j.tetlet.2013.12.105
Publication status	Published - 2014 Feb 5

Keywords

Alkyne
Cascade reaction
Copper-catalyzed
Oximes
Rearrangement

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis of 1,6-dihydropyrimidines via copper-catalyzed multistep cascade reactions between O-propargylic aldoximes and isocyanates",

abstract = "Multi-step cascade reactions of O-propargylic oximes with isocyanates were carried out in the presence of copper catalysts to afford the corresponding 1,6-dihydropyrimidines in good yields. The multi-step reactions consisted of a 2,3-rearrangement, a [3+2] cycloaddition, decarboxylative ring opening involving a 1,4-hydrogen shift, and a 6π-electrocyclization.",

keywords = "Alkyne, Cascade reaction, Copper-catalyzed, Oximes, Rearrangement",

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

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T1 - Synthesis of 1,6-dihydropyrimidines via copper-catalyzed multistep cascade reactions between O-propargylic aldoximes and isocyanates

AU - Nakamura, Itaru

AU - Onuma, Toshiki

AU - Zhang, Dong

AU - Terada, Masahiro

PY - 2014/2/5

Y1 - 2014/2/5

N2 - Multi-step cascade reactions of O-propargylic oximes with isocyanates were carried out in the presence of copper catalysts to afford the corresponding 1,6-dihydropyrimidines in good yields. The multi-step reactions consisted of a 2,3-rearrangement, a [3+2] cycloaddition, decarboxylative ring opening involving a 1,4-hydrogen shift, and a 6π-electrocyclization.

AB - Multi-step cascade reactions of O-propargylic oximes with isocyanates were carried out in the presence of copper catalysts to afford the corresponding 1,6-dihydropyrimidines in good yields. The multi-step reactions consisted of a 2,3-rearrangement, a [3+2] cycloaddition, decarboxylative ring opening involving a 1,4-hydrogen shift, and a 6π-electrocyclization.

KW - Alkyne

KW - Cascade reaction

KW - Copper-catalyzed

KW - Oximes

KW - Rearrangement

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