Phosphine-catalyzed [3+2] cycloaddition of phthalazinium dicyanomethanides with allenoates: highly efficient synthesis of 1,2,3,10b-tetrahydropyrrolo[2,1-a]phthalazine derivatives

被引:11
作者
Yuan, Chunhao [1 ]
Zhou, Leijie [1 ]
Sun, Zhanhu [1 ]
Guo, Hongchao [1 ]
机构
[1] China Agr Univ, Dept Appl Chem, Beijing 100193, Peoples R China
基金
中国国家自然科学基金; 高等学校博士学科点专项科研基金;
关键词
C; N-CYCLIC AZOMETHINE IMINES; ENANTIOSELECTIVE 4+1 ANNULATIONS; ELECTRON-DEFICIENT OLEFINS; ASYMMETRIC TOTAL-SYNTHESIS; FUNCTIONALIZED TETRAHYDROPYRIDINES; CHIRAL PHOSPHINES; AMINO-ACID; ORGANIC-SYNTHESIS; FORMAL SYNTHESES; FACILE ENTRY;
D O I
10.1039/c6ra13643e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The phosphine-catalyzed [3 + 2] cycloaddition between phthalazinium dicyanomethanides and allenoates, has been achieved in dichloromethane at room temperature, providing a broad range of novel heterocyclic compounds, 1,2,3,10b-tetrahydropyrrolo[2,1-a]phthalazine derivatives, as single (Z)-isomers in excellent yields (88-99% yield). All reactions are operationally simple and proceed very fast under mild reaction conditions.
引用
收藏
页码:77931 / 77936
页数:6
相关论文
共 91 条
[1]   Catalytic crossed Michael cycloisomerization of thioenoates:: Total synthesis of (±)-ricciocarpin A [J].
Agapiou, K ;
Krische, MJ .
ORGANIC LETTERS, 2003, 5 (10) :1737-1740
[2]   Enantioselective total synthesis of (+)-ibophyllidine via an asymmetric phosphine-catalyzed [3+2] annulation [J].
Andrews, Ian P. ;
Kwon, Ohyun .
CHEMICAL SCIENCE, 2012, 3 (08) :2510-2514
[3]   A Torquoselective 6π Electrocyclization Approach to Reserpine Alkaloids [J].
Barcan, Gregg A. ;
Patel, Ashay ;
Houk, K. N. ;
Kwon, Ohyun .
ORGANIC LETTERS, 2012, 14 (21) :5388-5391
[4]   Ionic liquids are compatible with on-water catalysis [J].
Beare, Kaitlin D. ;
Yuen, Alexander K. L. ;
Masters, Anthony F. ;
Maschmeyer, Thomas ;
McErlean, Christopher S. P. .
CHEMICAL COMMUNICATIONS, 2013, 49 (75) :8347-8349
[5]   A NEW ACCESS TO PHOSPHAINDOLIZINES BY [3+2] CYCLOADDITION OF AZOMETHINE YLIDES ONTO PHOSPHAALKYNES [J].
BERGSTRASSER, U ;
HOFFMANN, A ;
REGITZ, M .
TETRAHEDRON LETTERS, 1992, 33 (08) :1049-1052
[6]   Uncharacteristic thione behavior in a Huisgen cycloaddition reaction: a kinetic and theoretical study [J].
Butler, Richard N. ;
Coyne, Anthony G. ;
McArdle, Patrick ;
Sibley, Lisa M. ;
Burke, Luke A. .
TETRAHEDRON LETTERS, 2007, 48 (38) :6684-6687
[7]   Organic synthesis in water: 1,3-dipolar cycloaddition reactions at ambient temperature with aqueous suspensions of solid reactants [J].
Butler, Richard N. ;
Coyne, Anthony G. ;
Moloney, Eamon M. .
TETRAHEDRON LETTERS, 2007, 48 (20) :3501-3503
[8]   Water and Organic Synthesis: A Focus on the In-Water and On-Water Border. Reversal of the In-Water Breslow Hydrophobic Enhancement of the Normal endo-Effect on Crossing to On-Water Conditions for Huisgen Cycloadditions with Increasingly Insoluble Organic Liquid and Solid 2π-Dipolarophiles [J].
Butler, Richard N. ;
Coyne, Anthony G. ;
Cunningham, William J. ;
Moloney, Eamon M. .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (07) :3276-3291
[9]   Water and the Huisgen cycloaddition reaction:: A focus on polar contributions to the transition state in the reactions of dicyano(phthalazinium)methanide with substituted styrenes and benzylidene acetones [J].
Butler, RN ;
Coyne, AG ;
Cunningham, WJ ;
Moloney, EM ;
Burke, LA .
HELVETICA CHIMICA ACTA, 2005, 88 (07) :1611-1629
[10]   Kinetic and synthetic influences of water and solvent-free conditions on 1,3-dipolar cycloaddition reactions: the phthalazinium and pyridazinium dicyanomethanide 1,3-dipoles: surprisingly successful synthetic methods [J].
Butler, RN ;
Coyne, AG ;
Cunningham, WJ ;
Burke, LA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2002, (11) :1807-1815