Copper-Catalyzed Oxidative ipso-Cyclization of N-(p-Methoxyaryl)propiolamides with Disulfides and Water Leading to 3-(Arylthio)-1-azaspiro[4.5]deca-3,6,9-triene-2,8-diones

被引：37
作者：
Qian, Peng-Cheng [1 ,2 ]
Liu, Yu [1 ]
Song, Ren-Jie [1 ]
Xiang, Jian-Nan [1 ]
Li, Jin-Heng [1 ]
机构：
[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemobiosensing & Chemometr, Changsha 410082, Peoples R China
[2] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
来源：
SYNLETT | 2015年 / 26卷 / 09期
关键词：
copper; cyclization; N-(p-methoxyaryl)propiolamides; disulfides; 3-(arylthio)-1-azaspiro[4; 5]deca-3; 6; 9-triene-2; 8-diones; ELECTROPHILIC CYCLIZATION; DEAROMATIZATION; ALKYNES; HALOCYCLIZATION; SPIROCYCLIZATION; HETEROCYCLES; ALKYLATION; CHEMISTRY; PHENOLS;
D O I：
10.1055/s-0034-1380573
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new copper-catalyzed oxidative ipso-cyclization of N-(p-methoxyaryl)propiolamides with disulfides for the synthesis of 3-(arylthio)-1-azaspiro[4.5]deca-3,6,9-triene-2,8-diones has been developed. This method proceeds via sequential oxidative C-S bond formation, ipso-cyclization, and dearomatization and provides a new facile oxidative strategy to assemble the target products using an inexpensive catalytic system comprising copper(II) chloride and molecular oxygen.
引用
收藏
页码：1213 / 1216
页数：4
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