Synthesis of multisubstituted phenols by formal [4+2] cycloaddition of nucleophilic alkynes with 3-ethoxycyclobutanones

被引：12

作者：

Kuzuguchi, Takeo ^{[1
]}

Yabuuchi, Yuto ^{[1
]}

Yoshimura, Tomoyuki ^{[1
]}

Matsuo, Jun-ichi ^{[1
]}

机构：

[1] Kanazawa Univ, Grad Sch Med Sci, Div Pharmaceut Sci, Kakuma Machi, Kanazawa, Ishikawa 9201192, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 25期

关键词：

SUBSTITUTED PHENOLS; CYCLOBUTENONES; BENZANNULATION; DERIVATIVES; YNAMIDES; REARRANGEMENTS; CATALYSIS; CLEAVAGE; INDOLES; ALKENES;

D O I：

10.1039/c7ob00827a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nucleophilic alkynes bearing sulfonamide, trimethylsilyl, or p-methoxyphenyl groups at the sp carbon reacted with 3-ethoxycyclobutanones to give formal [4 + 2] cycloadducts by activation with TiCl4. Reactions with 2-monoalkyl and 2-nonsubstituted 3-ethoxycyclobutanones gave phenol derivatives directly by benzannulation, while the use of 2,2-dimethyl-3-ethoxycyclobutanone gave the corresponding dienones, which were converted to pentasubstituted phenols by dienone-phenol rearrangement. Regioselectivity that depended on the activation conditions of dienone-phenol rearrangement is also described.

引用

页码：5268 / 5271

页数：4

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