Radical Intramolecular Arylation of Pyridinium Salts: A Straightforward Entry to 7-Hydroxypyrido[2,1-a]isoquinolinylium Salts

被引:13
作者
Castillo, Rafael R. [1 ]
Burgos, Carolina [1 ]
Vaquero, Juan J. [1 ]
Alvarez-Builla, Julio [1 ]
机构
[1] Univ Alcala de Henares, Dept Quim Organ, E-28871 Alcala De Henares, Spain
关键词
Radical reactions; Nitrogen heterocycles; Intramolecular arylation; PROMOTED AROMATIC ALKYLATIONS; ARYL BROMIDES; CYCLIZATION; SUBSTITUTION; N-2'-PYRIDYLAMINIDE; TODDAQUINOLINE; ADDITIONS; BIARYLS;
D O I
10.1002/ejoc.201001071
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of 7-hydroxypyrido[2,1-a]isoquinolinylium salts can be achieved in moderate yields by intramolecular radical arylation of pyridinium salts obtained from substituted pyridines and o-bromophenacyl bromides.
引用
收藏
页码:619 / 628
页数:10
相关论文
共 53 条
[1]   A New Class of Pyrazolopyridine Nucleus with Fluorescent Properties, Obtained through Either a Radical or a Pd Arylation Pathway from N-Azinylpyridinium N-Aminides [J].
Abet, Valentina ;
Nunez, Araceli ;
Mendicuti, Francisco ;
Burgos, Carolina ;
Alvarez-Builla, Julio .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :8800-8807
[2]   Reactions of omega-substituted acetophenone derivatives. Part II. The mechanism of the interaction of omega-halogenoacetophenones with primary and tertiary bases. [J].
Baker, JW .
JOURNAL OF THE CHEMICAL SOCIETY, 1932, :1148-1157
[3]   Structure-activity relationship of isoform selective inhibitors of Rac1/1b GTPase nucleotide binding [J].
Beausoleil, Eric ;
Chauvignac, Cedric ;
Taverne, Thierry ;
Lacombe, Sandrine ;
Pognante, Laure ;
Leblond, Bertrand ;
Pallares, Diego ;
De Oliveira, Catherine ;
Bachelot, Florence ;
Carton, Rachel ;
Peillon, Helene ;
Coutadeur, Severine ;
Picard, Virginie ;
Lambeng, Nathalie ;
Desire, Laurent ;
Schweighoffer, Fabien .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (19) :5594-5598
[4]   Synthesis using aromatic homolytic substitution - recent advances [J].
Bowman, W. Russell ;
Storey, John M. D. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (11) :1803-1822
[5]   AROMATIC CYCLODEHYDRATION .43. SYNTHESIS OF TETRAHYDROBERBERINE AND SOME DEHYDROBERBERINE ANALOGS [J].
BRADSHER, CK ;
DUTTA, NL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (05) :1145-1147
[6]  
CARELLI V, 1967, ANN CHIM-ROME, V57, P269
[7]  
CASAGRANDE C, 1971, FARMACO-ED SCI, V26, P1059
[8]  
Chrobak E, 2004, HETEROCYCLES, V63, P2329
[9]   The generation and cyclisation of pyridinium radicals as a potential route to indolizidine alkaloids [J].
Dobbs, AP ;
Jones, K ;
Veal, KT .
TETRAHEDRON LETTERS, 1997, 38 (30) :5383-5386
[10]   QUINOLIZINES .9. PROPERTIES OF 3-HYDROXYQUINOLIZINIUM SALTS [J].
DUKE, PA ;
FOZARD, A ;
JONES, G .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (02) :526-&