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
收藏
页码：5268 / 5271
页数：4
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