Efficient solid-phase synthesis of 2,3-substituted indoles

被引：49

作者：

Wacker, DA ^{[1
]}

Kasireddy, P ^{[1
]}

机构：

[1] Bristol Myers Squibb Co, Expt Stn, Wilmington, DE 19880 USA

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 29期

关键词：

D O I：

10.1016/S0040-4039(02)01025-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The development of the solid-phase version of the modified Madelung indole synthesis is reported. The chemistry was initiated with the reductive amination of Bal resin using an ortho substituted aniline. The resin bound aniline was acylated with a variety of acid chlorides followed by cyclization with base to provide the desired indole after TFA-promoted cleavage from the resin. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5189 / 5191

页数：3

共 15 条

[1] The solid phase synthesis of tri-substituted indoles [J].

Collini, MD ;

Ellingboe, JW .

TETRAHEDRON LETTERS, 1997, 38 (46) :7963-7966

[2]

FISHER LE, 1993, Patent No. 5212195

[3]

FORBES IT, 1999, Patent No. 5922733

[4]

HENRY RT, 2000, Patent No. 616162818

[5] Application of polymer-bound phosphonium salts as traceless supports for solid phase synthesis [J].

Hughes, I .

TETRAHEDRON LETTERS, 1996, 37 (42) :7595-7598

[6] Fischer indole synthesis on a solid support [J].

Hutchins, SM ;

Chapman, KT .

TETRAHEDRON LETTERS, 1996, 37 (28) :4869-4872

[7] The solid-phase Nenitzescu indole synthesis [J].

Ketcha, DM ;

Wilson, LJ ;

Portlock, DE .

TETRAHEDRON LETTERS, 2000, 41 (33) :6253-6257

[8]

LUNN WHW, 1996, Patent No. 735821

[9] SYNTHESIS OF 3-SUBSTITUTED INDOLES VIA A MODIFIED MADELUNG REACTION [J].

ORLEMANS, EOM ;

SCHREUDER, AH ;

CONTI, PGM ;

VERBOOM, W ;

REINHOUDT, DN .

TETRAHEDRON, 1987, 43 (16) :3817-3826

[10] Traceless solid phase synthesis of 2,3-disubstituted indoles [J].

Smith, AL ;

Stevenson, GI ;

Swain, CJ ;

Castro, JL .

TETRAHEDRON LETTERS, 1998, 39 (45) :8317-8320

← 1 2 →