Synthesis of 3-iodoindoles by electrophilic cyclization of N,N-dialkyl-2-(1-alkynyl)anilines

被引：217

作者：

Yue, DW ^{[1
]}

Larock, RC ^{[1
]}

机构：

[1] Iowa State Univ Sci & Technol, Dept Chem, Ames, IA 50011 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 06期

关键词：

D O I：

10.1021/ol0498996

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A wide variety of N-alkyl-3-iodoindoles are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of N,N-dialkyl-o-iodoanilines and terminal alkynes, followed by electrophilic cyclization by I-2. Alkyl-, aryl-, and vinylic-substituted alkynes all undergo iodocyclization in excellent yields.

引用

页码：1037 / 1040

页数：4

共 61 条

[31] SYNTHESIS OF INDOLES VIA PALLADIUM-CATALYZED HETEROANNULATION OF INTERNAL ALKYNES [J].

LAROCK, RC ;

YUM, EK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (17) :6689-6690

[32] Palladium-catalyzed annulation [J].

Larock, RC .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :111-124

[33]

Li Jun, 2000, Proceedings of the CSEE, V20, P73

[34] Atropisomerism, biphenyls and the Suzuki coupling: peptide antibiotics [J].

Lloyd-Williams, P ;

Giralt, E .

CHEMICAL SOCIETY REVIEWS, 2001, 30 (03) :145-157

[35] PREPARATION OF VINBLASTINE, VINCRISTINE, AND LEUROSIDINE, ANTI-TUMOR ALKALOIDS FROM CATHARANTHUS SPP (APOCYNACEAE) [J].

MANGENEY, P ;

ANDRIAMIALISOA, RZ ;

LANGLOIS, N ;

LANGLOIS, Y ;

POTIER, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (08) :2243-2245

[36]

MANSKE RHF, 1959, ALKALOIDS J, V1

[37] Synthesis of nonracemic β-hydroxy ketones and carbonate derivatives from homopropargylic alcohols through iodolactonization [J].

Marshall, JA ;

Yanik, MM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :3798-3799

[38] 1,2-bis(1H-indol-3-yl)ethane-1,2-dione, an indole alkaloid from the marine sponge Smenospongia sp. [J].

McKay, MJ ;

Carroll, AR ;

Quinn, RJ ;

Hooper, JNA .

JOURNAL OF NATURAL PRODUCTS, 2002, 65 (04) :595-597

[39] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].

MIYAURA, N ;

SUZUKI, A .

CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483

[40] REACTIONS AND SYNTHETIC APPLICATIONS OF BETA-OXO-SULFOXIDES .6. NEW SYNTHESIS OF PYRIDO[4,3-B]CARBAZOLES OLIVACINE AND ELLIPTICINE [J].

OIKAWA, Y ;

YONEMITSU, O .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (13) :1479-1484

← 1 2 3 4 5 6 7 →