Synthesis of indoles using cyclization of imidoyl radicals

被引：18

作者：

Bowman, WR ^{[1
]}

Fletcher, AJ

Lovell, PJ

Pedersen, JM

机构：

[1] Univ Loughborough, Dept Chem, Loughborough LE11 3TU, Leics, England

[2] GlaxoSmithKline, Psychiat Med Chem 3, Harlow CM19 5AW, Essex, England

来源：

SYNLETT | 2004年 / 11期

关键词：

radicals; radical reactions; indoles; cyclizations; rearrangements;

D O I：

10.1055/s-2004-830868

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Imidoyl radicals, generated from imidoyl phenylselanide precursors, have been used for the synthesis of 2,3-disubstituted indoles. A facile high yielding synthesis of imidoyl phenylselanides has been developed. The potential for neophyl rearrangement of 5-exo radical intermediates to 6-endo radical intermediates is discussed.

引用

页码：1905 / 1908

页数：4

共 29 条

[21] FACILE PRODUCTION AND CYCLIZATIONS OF AMIDYL RADICALS [J].

NEWCOMB, M ;

ESKER, JL .

TETRAHEDRON LETTERS, 1991, 32 (08) :1035-1038

[22] An isonitrile-alkyne cascade to di-substituted indoles [J].

Rainier, JD ;

Kennedy, AR ;

Chase, E .

TETRAHEDRON LETTERS, 1999, 40 (35) :6325-6327

[23] Cascades to substituted indoles [J].

Rainier, JD ;

Kennedy, AR .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :6213-6216

[24]

Reding MT, 2002, HETEROCYCLES, V56, P313

[25] Stereocontrolled total synthesis of (±)-catharanthine via radical-mediated indole formation [J].

Reding, MT ;

Fukuyama, T .

ORGANIC LETTERS, 1999, 1 (07) :973-976

[26]

SU W, 2003, SYNLETT, P1299

[27]

Tokuyama H, 2001, SYNLETT, P1403

[28]

Tokuyama H, 2000, SYNTHESIS-STUTTGART, P429

[29] Radical cyclization of 2-alkenylthioanilides: A novel synthesis of 2,3-disubstituted indoles [J].

Tokuyama, H ;

Yamashita, T ;

Reding, MT ;

Kaburagi, Y ;

Fukuyama, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (15) :3791-3792

← 1 2 3 →