Efficient preparation of 2-substituted pyridazino[4,3-h]psoralen derivatives

被引:11
作者
González-Gómez, JC [1 ]
Uriarte, E [1 ]
机构
[1] Univ Santiago de Compostela, Fac Farm, Dept Quim Organ, Santiago De Compostela 15782, Spain
关键词
Diels-Alder; catalysis; DNA; palladium; polycycles;
D O I
10.1055/s-2003-42070
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
An efficient synthesis of 2-chloro-6-methoxypyridazino[4,3-h]psoralen was achieved by Diels-Alder reaction of 3,6-dichloro-1.2.4.5-tetrazine and 8-methoxy-psoralen (8-MOP) in a one-pot procedure. The convenient transformation of this intermediate into the 2-triflate derivative allowed efficient palladium-catalyzed reduction. methoxycarbonylation, and Sonogashira cross-coupling reactions at C-2.
引用
收藏
页码:2225 / 2227
页数:3
相关论文
共 37 条
[1]
Intramolecular inverse electron demand Diels-Alder reactions of tryptamine with tethered heteroaromatic azadienes [J].
Benson, SC ;
Lee, L ;
Yang, L ;
Snyder, JK .
TETRAHEDRON, 2000, 56 (09) :1165-1180
[3]
BRANA MR, 2001, CURR PHARM DESIGN, V8, P1405
[4]
Synthesis and cytotoxicity of potential anticancer derivatives of pyrazolo[3,4,5-kl]acridine and indolo[2,3-a]acridine [J].
Bu, XY ;
Chen, JJ ;
Deady, LW ;
Denny, WA .
TETRAHEDRON, 2002, 58 (01) :175-181
[5]
CACCHI S, 1990, ORG SYNTH, V68, P138
[6]
PALLADIUM-CATALYZED TRIETHYLAMMONIUM FORMATE REDUCTION OF ARYL TRIFLATES - A SELECTIVE METHOD FOR THE DEOXYGENATION OF PHENOLS [J].
CACCHI, S ;
CIATTINI, PG ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1986, 27 (45) :5541-5544
[7]
A convenient synthesis of psoralens [J].
Chimichi, S ;
Boccalini, M ;
Cosimelli, B ;
Viola, G ;
Vedaldi, D ;
Dall'Acqua, F .
TETRAHEDRON, 2002, 58 (24) :4859-4863
[8]
Dall'Acqua F., 1988, PHOTOMED PHOTOBIOL, V10, P1
[9]
New tetracyclic analogues of photochemotherapeutic drugs 5-MOP and 8-MOP: Synthesis, DNA interaction, and antiproliferative activity [J].
Dalla Via, L ;
Gia, O ;
Magno, SM ;
Santana, L ;
Teijeira, M ;
Uriarte, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (21) :4405-4413
[10]
A NEW 2-STEP PROCEDURE FOR FUNCTIONALIZED-3(2H)-PYRIDAZINONES THROUGH HOMOLYTIC SUBSTITUTION OF 3-CHLOROPYRIDAZINES [J].
DALPIAZ, V ;
GIOVANNONI, MP ;
CICIANI, G .
TETRAHEDRON LETTERS, 1993, 34 (24) :3903-3906