Rapid and efficient microwave-assisted synthesis of 4-, 5-, 6- and 7-azaindoles

被引：58

作者：

Lachance, N ^{[1
]}

April, M ^{[1
]}

Joly, MA ^{[1
]}

机构：

[1] Merck Frosst Ctr Therapeut Res, Pointe Claire, PQ H9R 4P8, Canada

来源：

SYNTHESIS-STUTTGART | 2005年 / 15期

关键词：

microwave; azaindole; pyrrolopyridine; palladium; Heck reaction;

D O I：

10.1055/s-2005-872100

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Under microwave irradiation conditions, the imines/ enamines formed between aminopyridines and ketones are converted in moderate to good yields to the corresponding 4-, 5-, 6- or 7-azaindoles via the Hegedus-Mori-Heck reaction (intrainolecular Heck reaction). A systematic examination of all isomeric azaindoles synthesis revealed this one-pot procedure to be general in scope.

引用

页码：2571 / 2577

页数：7

共 29 条

[1] TRYPTAMINES, CARBOLINES, AND RELATED COMPOUNDS .10. AN ALTERNATIVE SYNTHESIS, AND NITRATION, OF DELTA-CARBOLINE [J].

ABRAMOVITCH, RA ;

ADAMS, KAH .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1962, 40 (05) :864-&

[2] Compared reactivity of heterocyclic enaminones: Photochemical and palladium catalyzed synthesis of 6,7,8,9-tetrahydro-5H-pyrido[3,2-b]ind-9-ones [J].

Blache, Y ;

SinibaldiTroin, ME ;

Voldoire, A ;

Chavignon, O ;

Gramain, JC ;

Teulade, JC ;

Chapat, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) :8553-8556

[3] Heterocyclic enaminones:: Photochemical synthesis of 6,7,8,9-tetrahydro-5H-pyrido[2,3-b]indol-9-ones [J].

Blache, Y ;

Sinibaldi-Troin, ME ;

Hichour, M ;

Benezech, V ;

Chavignon, O ;

Gramain, JC ;

Teulade, JC ;

Chapat, JP .

TETRAHEDRON, 1999, 55 (07) :1959-1970

[4] Syntheses of indoles via a palladium-catalyzed annulation between iodoanilines and ketones [J].

Chen, CY ;

Lieberman, DR ;

Larsen, RD ;

Verhoeven, TR ;

Reider, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (09) :2676-2677

[5]

COUTURE A, 1993, SYNTHESIS-STUTTGART, P1227

[6] A CONVENIENT SYNTHESIS OF 6-AZAINDOLE [J].

FISHER, MH ;

MATZUK, AR .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1969, 6 (05) :775-&

[7] SYNTHESIS OF SUBSTITUTED 4- AND 6-AZAINDOLES [J].

FRYDMAN, B ;

REIL, SJ ;

BONED, J ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (10) :3762-&

[8] THE USE OF MICROWAVE-OVENS FOR RAPID ORGANIC-SYNTHESIS [J].

GEDYE, R ;

SMITH, F ;

WESTAWAY, K ;

ALI, H ;

BALDISERA, L ;

LABERGE, L ;

ROUSELL, J .

TETRAHEDRON LETTERS, 1986, 27 (03) :279-282

[9] APPLICATION OF COMMERCIAL MICROWAVE-OVENS TO ORGANIC-SYNTHESIS [J].

GIGUERE, RJ ;

BRAY, TL ;

DUNCAN, SM ;

MAJETICH, G .

TETRAHEDRON LETTERS, 1986, 27 (41) :4945-4948

[10] Recent developments in indole ring synthesis-methodology and applications [J].

Gribble, GW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07) :1045-1075

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