Reactions of Nitrosobenzenes with Cyclobutanones by Activation with a Lewis Acid

被引：5
作者：
Shima, Yusuke [1 ]
Igarashi, Emiko [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：
SYNLETT | 2018年 / 29卷 / 06期
关键词：
cyclobutanone; nitrosobenzene; cycloaddition; Lewis acid; carbon-carbon bond cleavage; hydroxamic acid; FORMAL 4+2 CYCLOADDITION; NITROSO ALDOL REACTION; DONOR-ACCEPTOR CYCLOBUTANES; SILYL ENOL ETHERS; CARBONYL-COMPOUNDS; HYDROXAMIC ACIDS; DELTA-LACTONES; ALDEHYDES; 3-ETHOXYCYCLOBUTANONES; CYCLOPROPANES;
D O I：
10.1055/s-0036-1588469
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Formal [4+2] cycloaddition between 3-ethoxy-2-alkylcy-clobutanones and nitrosobenzene proceeded by activation with Me-3-SiOTf to afford 6-alkyl-2-phenyl-2H-1,2-oxazin-5(6H)-one by regio-selective cleavage of the more substituted C2-C3 bond of the cyclobutanone ring. On the other hand, reactions of 3-phenylcyclobutanones and 2-benzyloxycyclobutanone with nitrosobenzene gave gamma,delta-unsaturated and cyclic hydroxamic acid derivatives, respectively, by cleavage of a cyclobutanone C1-C2 bond.
引用
收藏
页码：723 / 726
页数：4
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