Efficient synthesis of phenanthridinone derivatives via a palladium-catalyzed coupling process

被引:78
作者
Furuta, Takumi [1 ]
Kitamura, Yuki [1 ]
Hashimoto, Ayano [1 ]
Fujii, Satoshi [1 ]
Tanaka, Kiyoshi [1 ]
Kan, Toshiyuki [1 ]
机构
[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan
关键词
D O I
10.1021/ol062599z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-mediated domino reaction was developed to conveniently synthesize phenanthridinone derivatives. Phosphine ligand 1 strongly promotes the domino process, which includes aryl-aryl coupling and C-N bond formations concomitant with a deamidation reaction. The versatility and applicability to a broad range of substrates make this reaction useful for the development of bioactive derivatives.
引用
收藏
页码:183 / 186
页数:4
相关论文
共 13 条
[1]   Docking studies on PARP-1 inhibitors: insights into the role of a binding pocket water molecule [J].
Bellocchi, D ;
Macchiarulo, A ;
Costantino, G ;
Pellicciari, R .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (04) :1151-1157
[2]   Observations on the intramolecular Heck reactions of aromatic chlorides using palladium/imidazolium salts [J].
Caddick, S ;
Kofie, W .
TETRAHEDRON LETTERS, 2002, 43 (51) :9347-9350
[3]   A simple catalytic synthesis of condensed pyridones from o-bromoarylcarboxamides involving ipso substitution via palladacycles [J].
Ferraccioli, R ;
Carenzi, D ;
Motti, E ;
Catellani, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (03) :722-723
[4]  
Harayama T, 2002, SYNTHESIS-STUTTGART, P237
[5]   Synthesis of trisphaeridine and norchelerythrine through palladium-catalyzed aryl-aryl coupling reaction [J].
Harayama, T ;
Akamatsu, H ;
Okamura, K ;
Miyagoe, T ;
Akiyama, T ;
Abe, H ;
Takeuchi, Y .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (05) :523-528
[6]  
Hartwig JF, 1998, ANGEW CHEM INT EDIT, V37, P2046, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO
[7]  
2-L
[8]   4-Phenyl-1,2,3,6-tetrahydropyridine, an excellent fragment to improve the potency of PARP-1 inhibitors [J].
Ishida, J ;
Hattori, K ;
Yamamoto, H ;
Iwashita, A ;
Mihara, K ;
Matsuoka, N .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (19) :4221-4225
[9]   Synthesis of novel phenylnaphthyl phosphines and their applications to Pd-catalyzed intramolecular amidation [J].
Kitamura, Y ;
Hashimoto, A ;
Yoshikawa, S ;
Odaira, J ;
Furuta, T ;
Kan, T ;
Tanaka, K .
SYNLETT, 2006, (01) :115-117
[10]   Palladium-catalysed reactions of aryl halides with soft, non-organometallic nucleophiles [J].
Prim, D ;
Campagne, JM ;
Joseph, D ;
Andrioletti, B .
TETRAHEDRON, 2002, 58 (11) :2041-2075