Palladium-mediated total synthesis of 2-styrylbenzoic acids:: a general route to 2-azachrysenes

被引：9
作者：
Pampín, C
Estévez, JC
Castedo, L
Estévez, RJ
机构：
[1] Univ Santiago, CSIC, Dept Quim Organ, Santiago De Compostela 15782, Spain
[2] Univ Santiago, CSIC, Unidade Assoc, Santiago De Compostela 15782, Spain
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 25期
关键词：
D O I：
10.1016/S0040-4039(02)00731-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We describe a new total synthesis of 2-styrylbenzoic acids by Heck coupling of methyl o-iodobenzoates to styrenes. Additionally, in the first general synthesis of naphtho[2,1-f]isoquinolines, these acids were transformed into phenanthrenoic acids and thence into the target compounds by a six-step sequence including a Bischler-Napieralski cyclization. (C) 2002 Elsevier Science Ltd. All rights reserved.
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页码：4551 / 4553
页数：3
相关论文
共 38 条
[1]   FORMATION OF SOME 3-ARYL-3,4-DIHYDROISOCOUMARINS BY THERMAL RING-CLOSURE OF STILBENE-2-CARBOXYLIC ACIDS [J].
BELLINGER, GCA ;
CAMPBELL, WE ;
GILES, RGF ;
TOBIAS, JD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (12) :2819-2825
[2]   TRANSMISSION OF POLAR EFFECTS .21. ALKALINE-HYDROLYSIS OF THE 2'-SUBSTITUTED AND 4'-SUBSTITUTED 2-METHOXYCARBONYLDIPHENYLACETYLENES AND (Z)-2'-SUBSTITUTED AND (Z)-4'-SUBSTITUTED 2-METHOXYCARBONYLSTILBENES AND THE IONIZATION AND ESTERIFICATION, WITH DIAZODIPHENYLMETHANE OF THE ACIDS OF THE LATTER SERIES [J].
BOWDEN, K ;
GHADIR, KDF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (08) :1333-1338
[3]   RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION [J].
CABRI, W ;
CANDIANI, I .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :2-7
[4]   AROMATIC CARBOXYLIC-ACIDS AS LATENT AROMATIC KETONES - NEW REGIOSELECTIVE SYNTHESIS OF AROMATIC KETONES [J].
CALUWE, P ;
PEPPER, T .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1786-1790
[5]   Azaarenes in the aerosol of an urban atmosphere [J].
Chen, HY ;
Preston, MR .
ENVIRONMENTAL SCIENCE & TECHNOLOGY, 1998, 32 (05) :577-583
[6]  
Chen JX, 1998, CANCER RES, V58, P2070
[7]  
Cheng C C, 1988, Prog Med Chem, V25, P35, DOI 10.1016/S0079-6468(08)70277-7
[8]  
CITTERIO A, 1990, SYNTHESIS-STUTTGART, P142
[9]   Preferential formation of benzo[a]pyrene adducts at lung cancer mutational hotspots in P53 [J].
Denissenko, MF ;
Pao, A ;
Tang, MS ;
Pfeifer, GP .
SCIENCE, 1996, 274 (5286) :430-432
[10]   Cytosine methylation determines hot spots of DNA damage in the human P53 gene [J].
Denissenko, MF ;
Chen, JX ;
Tang, MS ;
Pfeifer, GP .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1997, 94 (08) :3893-3898
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