Synthesis of indolo[1,2-f]phenanthridines from palladium-catalyzed reactions of arynes

被引：88

作者：

Xie, Chunsong ^{[1
]}

Zhang, Yuhong ^{[1
]}

Huang, Zedu ^{[1
]}

Xu, Peixin ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 14期

关键词：

D O I：

10.1021/jo070625g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel convenient approach for the construction of indolo[1,2- f]phenanthridine was developed from the reaction of arynes with 1-(2-bromophenyl)-1H-indole in the presence of palladium catalyst.

引用

页码：5431 / 5434

页数：4

共 52 条

[1] Electrochemical assembling/disassembling of helicates with hysteresis [J].

Amendola, V ;

Fabbrizzi, L ;

Gianelli, L ;

Maggi, C ;

Mangano, C ;

Pallavicini, P ;

Zema, M .

INORGANIC CHEMISTRY, 2001, 40 (14) :3579-3587

[2] Isolation of drugs active against mammalian prions using a yeast-based screening assay [J].

Bach, S ;

Talarek, N ;

Andrieu, T ;

Vierfond, JM ;

Mettey, Y ;

Galons, H ;

Dormont, D ;

Meijer, L ;

Cullin, C ;

Blondel, M .

NATURE BIOTECHNOLOGY, 2003, 21 (09) :1075-1081

[3] Synthesis of quinolines, 2-quinolones, phenanthridines, and 6(5H)-phenanthridinones via palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitroarenes with β-halo-enals, -enones, or -esters [J].

Banwell, MG ;

Lupton, DW ;

Ma, XH ;

Renner, J ;

Sydnes, MO .

ORGANIC LETTERS, 2004, 6 (16) :2741-2744

[4] Distinct mechanisms for the oxidative addition of chloro-, bromo-, and lodoarenes to a bisphosphine palladium(0) complex with hindered ligands [J].

Barrios-Landeros, F ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) :6944-6945

[5] Picosecond dynamics of singlet excited states of oxotetrahydrobenzo[c]phenanthridine in protic and aprotic solvents [J].

Bondarev, S. L. ;

Knyukshto, V. N. ;

Tikhomirov, S. A. ;

Pyrko, A. N. .

OPTICS AND SPECTROSCOPY, 2006, 100 (03) :386-393

[6] CARCINOGENIC NITROGEN COMPOUNDS .21. NEW ALKYL HOMOLOGUES OF PHENANTHRIDINE, BENZACRIDINES, AND RELATED NUCLEI [J].

BUUHOI, NP ;

JACQUIGNON, P ;

LONG, CT .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (FEB) :505-509

[7] Novel potent and selective central 5-HT3 receptor ligands provided with different intrinsic efficacy.: 1.: Mapping the central 5-HT3 receptor binding site by arylpiperazine derivatives [J].

Cappelli, A ;

Anzini, M ;

Vomero, S ;

Mennuni, L ;

Makovec, F ;

Doucet, E ;

Hamon, M ;

Bruni, G ;

Romeo, MR ;

Menziani, MC ;

De Benedetti, PG ;

Langer, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (05) :728-741

[8] Catalytic carbonylation reactions of benzyne derivatives [J].

Chatani, N ;

Kamitani, A ;

Oshita, M ;

Fukumoto, Y ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (50) :12686-12687

[9] Regioselective [2+2+2] cycloaddition of a nickel-benzyne complex with 1,3-diynes [J].

Deaton, KR ;

Gin, MS .

ORGANIC LETTERS, 2003, 5 (14) :2477-2480

[10] Design and synthesis of poly ADP-ribose polymerase-1 inhibitors.: 2.: Biological evaluation of aza-5[H]-phenanthridin-6-ones as potent, aqueous-soluble compounds for the treatment of ischemic injuries [J].

Ferraris, D ;

Ko, YS ;

Pahutski, T ;

Ficco, RP ;

Serdyuk, L ;

Alemu, C ;

Bradford, C ;

Chiou, T ;

Hoover, R ;

Huang, S ;

Lautar, S ;

Liang, S ;

Lin, QA ;

Lu, MXC ;

Mooney, M ;

Morgan, L ;

Qian, YZ ;

Tran, S ;

Williams, LR ;

Wu, QY ;

Zhang, J ;

Zou, YN ;

Kalish, V .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (14) :3138-3151

← 1 2 3 4 5 6 →