Cascade approach to substituted 6-aryl-phenanthridines from aromatic aldehydes, anilines, and benzenediazonium-2-carboxylate

被引：94

作者：

Shou, Wang-Ge ^{[1
]}

Yang, Yun-Yun ^{[1
]}

Wang, Yan-Guang ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 24期

关键词：

D O I：

10.1021/jo061648i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Aromatic aldehydes reacted with anilines and benzenediazonium-2-carboxylate to afford 6-aryl-phenanthridines. The reaction furnishes a rapid and direct construction of substituted phenanthridine rings from readily available starting materials via a one-pot cascade process.

引用

页码：9241 / 9243

页数：3

共 55 条

[1] Reaction of diimines and benzyne [J].

Aly, AA ;

Mohamed, NK ;

Hassan, AA ;

Mourad, AFE .

TETRAHEDRON, 1999, 55 (04) :1111-1118

[2] 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

[3] POTENTIAL ANTITUMOR AGENTS .55. 6-PHENYLPHENANTHRIDINE-4-CARBOXAMIDES - A NEW CLASS OF DNA-INTERCALATING ANTITUMOR AGENTS [J].

ATWELL, GJ ;

BAGULEY, BC ;

DENNY, WA .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (04) :774-779

[4] 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

[5] 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

[6]

BEIHL ER, 1989, ACCOUNTS CHEM RES, V22, P275

[7] Synthesis of 2,3-dihydroindoles, indoles, and anilines by transition metal-free amination of aryl chlorides [J].

Beller, M ;

Breindl, C ;

Riermeier, TH ;

Tillack, A .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1403-1412

[8] 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

[9] 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

[10] 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

← 1 2 3 4 5 6 →