Synthesis of naphthalenes through three-component coupling of alkynes, Fischer carbene complexes, and benzaldehyde hydrazones via isoindole intermediates

被引:55
作者
Duan, Shaofeng [1 ]
Sinha-Mahapatra, Dilip K. [1 ]
Herndon, James W. [1 ]
机构
[1] New Mexico State Univ, Dept Chem & Biochem, Las Cruces, NM 88003 USA
关键词
D O I
10.1021/ol800242n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of naphthalene derivatives through three-component coupling of 2-alkynylbenzaidehyde hydrazones with carbene complexes and electron-deficient alkynes has been examined. The reaction involves formation of an isoindole derivative, followed by intramolecular Diels-Alder reaction, followed by nitrene extrusion. The reaction was highly regioselective using unsymmetrical alkynes.
引用
收藏
页码:1541 / 1544
页数:4
相关论文
共 26 条
[1]  
ANIKINA LV, 2002, PHARM CHEM J, V36, P72
[2]  
ARISVARAN V, 1981, SYNTHESIS-STUTTGART, P821
[3]  
Banfi L, 2007, CURR OPIN DRUG DISC, V10, P704
[4]   Group 6 Fischer carbene complexes:: "chemical multitalents" for multi-component reactions [J].
Barluenga, J ;
Fernández-Rodríguez, MA ;
Aguilar, E .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (03) :539-587
[5]   EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION [J].
BORDWELL, FG .
ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) :456-463
[6]   Oxadisilole-fused isoindole [J].
Chen, Ya-Li ;
Lee, Man-Ho ;
Wong, Wai-Yeung ;
Lee, Albert W. M. .
SYNLETT, 2006, (15) :2510-2512
[7]   Syntheses of soluble, π-stacking tetracene derivatives [J].
Chen, ZH ;
Muller, P ;
Swager, TM .
ORGANIC LETTERS, 2006, 8 (02) :273-276
[8]   Expedient synthesis and structure-activity relationships of phenanthroindolizidine and phenanthroquinolizidine alkaloids [J].
Chuang, TH ;
Lee, SJ ;
Yang, CW ;
Wu, PL .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (05) :860-867
[9]   Highly selective diels-alder reactions of directly connected enyne dienophiles [J].
Dai, Mingji ;
Sarlah, David ;
Yu, Maolin ;
Danishefsky, Samuel J. ;
Jones, Gavin O. ;
Houk, K. N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (03) :645-657
[10]   Modern methods for the synthesis of substituted naphthalenes [J].
de Koning, CB ;
Rousseau, AL ;
van Otterlo, WAL .
TETRAHEDRON, 2003, 59 (01) :7-36