Highly Efficient Access to Iminoisocoumarins and α-Iminopyrones via AgOTf-Catalyzed Intramolecular Enyne-Amide Cyclization

被引:54
作者
Bian, Ming [1 ]
Yao, Weijun [1 ]
Ding, Hanfeng [1 ]
Ma, Cheng [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
关键词
NITROGEN DOUBLE-BOND; TERMINAL ACETYLENES; ISOMERIZATION; ALKYNES; HETEROCYCLES; CHEMISTRY; ACID; OXAZOLES; IMINES; RULES;
D O I
10.1021/jo9023478
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Iminoisocoumarins and alpha-iminopyrones are prepared via Sonogashira coupling and AgOTf-catalyzed 6-endo-dig O-cyclization of the enyne-amide system in dichloroethane, in one pot or stepwise, respectively.
引用
收藏
页码:269 / 272
页数:4
相关论文
共 35 条
[1]   Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[2]   Silver-mediated synthesis of heterocycles [J].
Alvarez-Corral, Miriam ;
Munoz-Dorado, Manuel ;
Rodirguez-Garcia, Ignacio .
CHEMICAL REVIEWS, 2008, 108 (08) :3174-3198
[3]   Preparation of 2,5-disubstituted oxazoles from N-propargylamides [J].
Arcadi, A ;
Cacchi, S ;
Cascia, L ;
Fabrizi, G ;
Marinelli, F .
ORGANIC LETTERS, 2001, 3 (16) :2501-2504
[4]   RULES FOR RING-CLOSURE [J].
BALDWIN, JE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736
[5]   Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].
Beller, M ;
Seayad, J ;
Tillack, A ;
Jiao, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398
[6]   Gallium(III) chloride-catalyzed double insertion of isocyanides into epoxides [J].
Bez, G ;
Zhao, CG .
ORGANIC LETTERS, 2003, 5 (26) :4991-4993
[7]  
Cacchi S, 1999, SYNLETT, P401
[8]   Novel and efficient synthesis of iminocoumarins via copper-catalyzed multicomponent reaction [J].
Cui, Sun-Liang ;
Lin, Xu-Feng ;
Wang, Yan-Guang .
ORGANIC LETTERS, 2006, 8 (20) :4517-4520
[9]   Cis-trans isomerization of organic molecules and biomolecules: Implications and applications [J].
Dugave, C ;
Demange, L .
CHEMICAL REVIEWS, 2003, 103 (07) :2475-2532
[10]   Optimization of an imidate hydrolysis reaction: Use of DOE and mathematical modeling to deliver yield and productivity improvements [J].
Gavin, DJ ;
Mojica, CA .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (06) :659-664