Platinum-catalyzed Tandem Carboalkoxylation-Claisen Rearrangement of Arylalkynes Bearing an ortho-1,5-Dihydro-3H-2,4-dioxepine Group
Platinum-catalyzed Tandem Carboalkoxylation-Claisen Rearrangement of Arylalkynes Bearing an ortho-1,5-Dihydro-3H-2,4-dioxepine Group
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DOI：
10.1246/cl.2005.174
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发表时间：
2005-01
影响因子：
1.6
通讯作者：
I. Nakamura;G. B. Bajracharya;Yoshinori Yamamoto
中科院分区：
文献类型：
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作者：
I. Nakamura;G. B. Bajracharya;Yoshinori Yamamoto
含邻位1，5-二氢-3H-2，4-二氧杂环庚烯基的芳基炔1在铂催化下进行烷氧羰基化-Claisen重排反应，得到相应的三环化合物2。例如，2-[2-（2-甲氧基苯基）-2-甲基-3-氧代-4-甲基-2-氧代-4-氧（1-（2-甲氧基苯基）氨基）乙基）氨基）苯基）-4，7-二氢[1，3]二氧杂卓（辛-1-炔基）苯基]-4，7-二氢[1，3]二氧杂环庚三烯1c和2-[2-（苯乙炔基）苯基]-4，7-二氢[1，3]二氧杂环庚三烯1d在100 ℃、10mol%PtCl2和40mol% β-蒎烯的乙腈溶液中反应，得到相应的三环化合物2a、2c和2d，63和50%的产率。
The platinum-catalyzed tandem carboalkoxylation-Claisen rearrangement reaction of arylalkynes 1 bearing an ortho-1,5-di-hydro-3H-2,4-dioxepine group gave the corresponding tricyclic compounds 2 in good to allowable yields. For example, the reaction of 2-[2-(pent-1-ynyl)phenyl]-4,7-dihydro[1,3]dioxepin la, 2-[2-(oct-1-ynyl)phenyl]-4,7-dihydro[1,3]dioxepin 1c, and 2-[2-(phenylethynyl)phenyl]-4,7-dihydro[1,3]dioxepin 1d in the presence of 10 mol % of PtCl 2 and 40 mol % of β-pinene in acetonitrile at 100°C gave the corresponding tricyclic compounds 2a, 2c, and 2d in 69, 63, and 50% yields, respectively.