Facile Synthesis of Polycyclic Fluorene Derivatives via a Palladium-Catalyzed Coupling, Propargyl-Allenyl Isomerization and Schmittel Cyclization Sequence

被引:28
作者
Shen, Ruwei [1 ]
Chen, Linzhu [1 ]
Huang, Xian [1 ,2 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Peoples R China
[2] 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
allenes; fluorenes; Schmittel cyclization; sequential reactions; FORMAL DIELS-ALDER; ENYNE-ALLENES; MYERS-SAITO; C-2-C-6; CYCLIZATION; DOMINO REACTIONS; BIRADICAL CYCLIZATION; NATURAL-PRODUCTS; TANDEM REACTIONS; ENE REACTION; SWITCH;
D O I
10.1002/adsc.200900600
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A stepwise process involving Sonogashira coupling, propargyl-allenyl isomerization and Schmittel cyclization has been realized, leading to an efficient synthesis of polycyclic fluorene derivatives from readily available starting materials. The reaction features the formation of three new carbon-carbon bonds to construct the benzene unit together with an efficient assembly of three or four rings in a single operative step.
引用
收藏
页码:2833 / 2838
页数:6
相关论文
共 71 条
[1]   FLUORENE DERIVATIVES FOR ANTITUMOR ACTIVITY [J].
AGRAWAL, KC .
JOURNAL OF MEDICINAL CHEMISTRY, 1967, 10 (01) :99-&
[2]   Cascading pericyclic reactions: building complex carbon frameworks for natural product synthesis [J].
Arns, Steve ;
Barriault, Louis .
CHEMICAL COMMUNICATIONS, 2007, (22) :2211-2221
[3]  
BERNIUS M, 2000, J MATER SCI, V35, P111
[4]  
Braun PU, 2000, ORG LETT, V2, P4181
[5]   Coupling-isomerization synthesis of chalcones [J].
Braun, Roland U. ;
Ansorge, Markus ;
Mueller, Thomas J. J. .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (35) :9081-9094
[6]   A novel one-pot pyrrole synthesis via a coupling-isomerization-Stetter-Paal-knorr sequence [J].
Braun, RU ;
Zeitler, K ;
Muller, TJJ .
ORGANIC LETTERS, 2001, 3 (21) :3297-3300
[7]  
BRUCH M, 1976, LIEBIGS ANN CHEM, P74
[8]   Oxyanion-accelerated C2-C6 cyclization of benzannulated enyne-allenes [J].
Brunette, SR ;
Lipton, MA .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (17) :5114-5119
[9]   ALKYLATION OF AROMATIC NUCLEUS .6. FLUORENE [J].
CAIRNS, JF ;
HICKINBOTTOM, WJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1962, (MAR) :867-&
[10]   Seongomycin: A new sulfur-containing benzo[b]fluorene derived from genes clustered with those for kinamycin biosynthesis [J].
Carney, JR ;
Hong, ST ;
Gould, SJ .
TETRAHEDRON LETTERS, 1997, 38 (18) :3139-3142