Toward safer methodologies for the synthesis of polyheterocyclic systems:: intramolecular arylation of arenes under Mizoroki-Heck reaction conditions

被引:50
作者
Hernández, S [1 ]
SanMartin, R [1 ]
Tellitu, I [1 ]
Domínguez, E [1 ]
机构
[1] Euskal Herriko Unibertsitatea, Kimika Organikoa Saila 2, Zientzi Fak, Bilbao 48080, Spain
关键词
D O I
10.1021/ol034148+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHIC] A straightforward synthesis of ibudilast-related pyrazolo[1,5-f]phenanthridines is accomplished by a tandem amine-exchange/heterocyclization of arylenaminones followed by an intramolecular biaryl coupling of the so-formed diarylpyrazoles. The direct, environmentally convenient ring-closure of the latter pyrazole intermediates, which show a close resemblance to the antiinflammatory drug celecoxib, is efficiently performed under Mizoroki-Heck reaction conditions.
引用
收藏
页码:1095 / 1098
页数:4
相关论文
共 55 条
[41]   Direct homocoupling of aryl halides catalyzed by palladium [J].
Penalva, V ;
Hassan, J ;
Lavenot, L ;
Gozzi, C ;
Lemaire, M .
TETRAHEDRON LETTERS, 1998, 39 (17) :2559-2560
[42]  
REINER PB, 2002, Patent No. 20020037843
[43]   Alternative and mild procedures for the removal of organotin residues from reaction mixtures [J].
Renaud, P ;
Lacôte, E ;
Quaranta, L .
TETRAHEDRON LETTERS, 1998, 39 (15) :2123-2126
[44]   Potentiation of ibudilast inhibition of platelet aggregation in the presence of endothelial cells [J].
Rile, G ;
Yatomi, Y ;
Qi, RM ;
Satoh, K ;
Ozaki, Y .
THROMBOSIS RESEARCH, 2001, 102 (03) :239-246
[45]   TOWARDS NONPOLLUTING ORGANOTIN REAGENTS FOR SYNTHESIS [J].
RUEL, G ;
DUMARTIN, G ;
DELMOND, B ;
LALERE, B ;
DONARD, OFX ;
PEREYRE, M .
APPLIED ORGANOMETALLIC CHEMISTRY, 1995, 9 (07) :591-595
[46]   Highly diastereoselective synthesis of propargylic 1,2-anti-diol derivatives using α-alkoxypropargylstannanes [J].
Savall, BM ;
Powell, NA ;
Roush, WR .
ORGANIC LETTERS, 2001, 3 (19) :3057-3060
[47]   A prospective randomized safety trial of celecoxib for treatment of preterm labor [J].
Stika, CS ;
Gross, GA ;
Leguizamon, G ;
Gerber, S ;
Levy, R ;
Mathur, A ;
Bernhard, LM ;
Nelson, DM ;
Sadovsky, Y .
AMERICAN JOURNAL OF OBSTETRICS AND GYNECOLOGY, 2002, 187 (03) :653-660
[48]   Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995-1998 [J].
Suzuki, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :147-168
[49]   Ibudilast attenuates astrocyte apoptosis via cyclic GMP signalling pathway in an in vitro reperfusion model [J].
Takuma, K ;
Lee, E ;
Enomoto, R ;
Mori, K ;
Baba, A ;
Matsuda, T .
BRITISH JOURNAL OF PHARMACOLOGY, 2001, 133 (06) :841-848
[50]  
TSUJI J, 2000, TRANSITION METAL REA, P94