New versatile route to the synthesis of tetrahydro-β-carbolines and tetrahydro-pyrano[3,4-b]indoles via an intramolecular Michael addition catalyzed by InBr3

被引：84

作者：

Agnusdei, M ^{[1
]}

Bandini, M ^{[1
]}

Melloni, A ^{[1
]}

Umani-Ronchi, A ^{[1
]}

机构：

[1] Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 18期

关键词：

D O I：

10.1021/jo034466m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple multistep synthetic strategy to 4-substituted 1,2,3,4-tetrahydro-beta-carboline and 1,3,4,9-tetrahydro-pyrano[3,4-b]indole derivatives starting from commercially available indole 2-carboxylic acid (5) is described. The final intramolecular Michael addition promoted by catalytic amount of InBr3 (5-10 mol %) provided the expected polycyclic compounds in excellent yields (up to 97%) both in anhydrous organic and aqueous media.

引用

页码：7126 / 7129

页数：4

共 24 条

[1]

Bandini M, 2003, SYNTHESIS-STUTTGART, P397

[2] InBr3-catalyzed friedel-crafts addition of indoles to chiral aromatic epoxides:: A facile route to enantiopure indolyl derivatives [J].

Bandini, M ;

Cozzi, PG ;

Melchiorre, P ;

Umani-Ronchi, A .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5386-5389

[3] A practical indium tribromide catalysed addition of indoles to nitroalkenes in aqueous media [J].

Bandini, M ;

Melchiorre, P ;

Melloni, A ;

Umani-ronchi, A .

SYNTHESIS-STUTTGART, 2002, (08) :1110-1114

[4] Sequential one-pot InBr3-catalyzed 1,4-then 1,2-nucleophilic addition to enones [J].

Bandini, M ;

Cozzi, PG ;

Giacomini, M ;

Melchiorre, P ;

Selva, S ;

Umani-Ronchi, A .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) :3700-3704

[5] 4-trifloxy-9-SEM-β-carboline:: Preparation and synthetic utility [J].

Busacca, CA ;

Eriksson, MC ;

Dong, Y ;

Prokopowicz, AS ;

Salvagno, AM ;

Tschantz, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4564-4568

[6] Advances in indium-catalysed organic synthesis [J].

Chauhan, KK ;

Frost, CG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (18) :3015-3019

[7] Synthesis and evaluation of analogues of the partial agonist 6-(propyloxy)-4-(methoxymethyl)-β-carboline-3-carboxylic acid ethyl ester (6-PBC) and the full agonist 6-(benzyloxy)-4-(methoxymethyl)-β-carboline-3-carboxylic acid ethyl ester (Zk 93423) at wild type and recombinant GABAA receptors [J].

Cox, ED ;

Diaz-Arauzo, H ;

Huang, Q ;

Reddy, MS ;

Ma, CR ;

Harris, B ;

McKernan, R ;

Skolnick, P ;

Cook, JM .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (14) :2537-2552

[8] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].

COX, ED ;

COOK, JM .

CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842

[9] A general procedure for a one-pot oxidative cleavage/Wittig reaction of glycols [J].

Dunlap, NK ;

Mergo, W ;

Jones, JM ;

Carrick, JD .

TETRAHEDRON LETTERS, 2002, 43 (21) :3923-3925

[10] Palladium-catalyzed acylation of a 1,2-disubstituted 3-indolylzinc chloride [J].

Faul, MM ;

Winneroski, LL .

TETRAHEDRON LETTERS, 1997, 38 (27) :4749-4752

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