Thermal induced intramolecular [2+2] cycloaddition of allene-ACPs

被引:32
作者
Chen, Kai [1 ,2 ]
Sun, Run [1 ,2 ]
Xu, Qin [1 ,2 ]
Wei, Yin [3 ]
Shi, Min [1 ,2 ,3 ]
机构
[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China
[2] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
UNIQUE TETRASUBSTITUTED ALKENE; MGI2-MEDIATED RING EXPANSIONS; ACID-MEDIATED CYCLOADDITION; TETHERED ALKYLIDENECYCLOPROPANES; CYCLOBUTANE DERIVATIVES; PYRROLIDINE SKELETONS; BOND-CLEAVAGE; METHYLENECYCLOPROPANES; EFFICIENT; LEWIS;
D O I
10.1039/c3ob40911b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile synthetic method for preparation of bicyclo[4.2.0] nitrogen heterocycles has been developed via a thermal induced intramolecular [2 + 2] cycloaddition reaction of allene-ACPs. The DFT calculations indicate that this intramolecular cycloaddition proceeds in a concerted manner and a strained small ring is essential.
引用
收藏
页码:3949 / 3953
页数:5
相关论文
共 69 条
[1]   Ruthenium-Catalyzed Hydroarylation of Methylenecyclopropanes through C-H Bond Cleavage: Scope and Mechanism [J].
Ackermann, Lutz ;
Kozhushkov, Sergei I. ;
Yufit, Dmitry S. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (38) :12068-12077
[2]   A rhodium-catalyzed C-H activation/cycloisomerization tandem [J].
Aissa, Christophe ;
Fuerstner, Alois .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (48) :14836-+
[3]   Exploiting [2+2] cycloaddition chemistry: achievements with allenes [J].
Alcaide, Benito ;
Almendros, Pedro ;
Aragoncillo, Cristina .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :783-816
[4]  
[Anonymous], CHEM REV
[5]  
[Anonymous], CARBOCYCLIC 3 4 MEMB
[6]  
[Anonymous], SYNTHESIS
[7]  
[Anonymous], EUR J ORG CHEM
[8]  
[Anonymous], EUR J ORG CHEM
[9]   Synthesis of Methylene- and Alkylidenecyclopropane Derivatives [J].
Audran, Gerard ;
Pellissier, Helene .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (04) :575-608
[10]   Heterocycles from alkylidenecyclopropanes [J].
Brandi, A ;
Cicchi, S ;
Cordero, FM ;
Goti, A .
CHEMICAL REVIEWS, 2003, 103 (04) :1213-1269