Solvent dependent Bergman cyclization of 2,3-diethynylquinoxaline

被引:25
作者
Kim, CS [1 ]
Russell, KC [1 ]
机构
[1] Univ Miami, Dept Chem, Coral Gables, FL 33124 USA
关键词
D O I
10.1016/S0040-4039(99)00634-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Kinetics of thermocyclization of 2,3-diethynylquinoxaline have been studied in various solvents. The cyclization rates observed were surprisingly solvent dependent. The half-lives varied from 361 in CH3CN to 16 min in THF. The half-life data show a good correlation with the solvents' spectroscopic E-T(30) values and dielectric constants. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3835 / 3838
页数:4
相关论文
共 17 条
[1]   REACTIVE 1,4-DEHYDROAROMATICS [J].
BERGMAN, RG .
ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (01) :25-31
[2]  
Dean J.A., Lange's Handbook of Chemistry
[3]   THE STRUCTURE OF NEOCARZINOSTATIN CHROMOPHORE POSSESSING A NOVEL BICYCLO-[7,3,0]DODECADIYNE SYSTEM [J].
EDO, K ;
MIZUGAKI, M ;
KOIDE, Y ;
SETO, H ;
FURIHATA, K ;
OTAKE, N ;
ISHIDA, N .
TETRAHEDRON LETTERS, 1985, 26 (03) :331-334
[4]   ESPERAMICINS, A NOVEL CLASS OF POTENT ANTITUMOR ANTIBIOTICS .2. STRUCTURE OF ESPERAMICIN-X [J].
GOLIK, J ;
CLARDY, J ;
DUBAY, G ;
GROENEWOLD, G ;
KAWAGUCHI, H ;
KONISHI, M ;
KRISHNAN, B ;
OHKUMA, H ;
SAITOH, K ;
DOYLE, TW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3461-3462
[5]   HIGH-TEMPERATURE RADICAL CYCLIZATION ANOMALIES IN THE TANDEM ENEDIYNE-BIS-RADICAL CYCLIZATION [J].
GRISSOM, JW ;
CALKINS, TL ;
HUANG, DH ;
MCMILLEN, H .
TETRAHEDRON, 1994, 50 (16) :4635-4650
[6]   Rapid Bergman cyclization of 1,2-diethynylheteroarenes [J].
Kim, CS ;
Russell, KC .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8229-8234
[7]   CALICHEMICINS, A NOVEL FAMILY OF ANTITUMOR ANTIBIOTICS .1. CHEMISTRY AND PARTIAL STRUCTURE OF CALICHEMICIN-GAMMA-1 [J].
LEE, MD ;
DUNNE, TS ;
SIEGEL, MM ;
CHANG, CC ;
MORTON, GO ;
BORDERS, DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3464-3466
[8]  
MAIER ME, 1992, LIEBIGS ANN CHEM, P855
[9]  
MASATAKA K, 1989, J ANTIBIOT, V42, P1449
[10]   DNA CLEAVAGE BY A SYNTHETIC MIMIC OF THE CALICHEAMICIN ESPERAMICIN CLASS OF ANTIBIOTICS [J].
NICOLAOU, KC ;
OGAWA, Y ;
ZUCCARELLO, G ;
KATAOKA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (21) :7247-7248