A tandem cross-coupling/SNAr approach to functionalized carbazoles

被引：65

作者：

Jean, David J. St., Jr. ^{[1
]}

Poon, Steve F. ^{[1
]}

Schwarzbach, Jamie L. ^{[1
]}

机构：

[1] Amgen Inc, Dept Med Chem, Thousand Oaks, CA 91320 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 23期

关键词：

D O I：

10.1021/oI702274y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel route to functionalized carbazoles utilizing a tandem Suzuki cross-coupling/SNAr protocol is described. This process was found to be compatible with a variety of electron-withdrawing groups including aldehydes, esters, and sulfones. Using this method, a concise total synthesis (four steps, 50% overall yield) of the carbazole alkaloid glycosinine was achieved.

引用

页码：4893 / 4896

页数：4

共 30 条

[1] Deprotection of N-tosylated indoles and related structures using cesium carbonate [J].

Bajwa, Joginder S. ;

Chen, Guang-Pei ;

Prasad, Kapa ;

Repic, Jan ;

Blacklock, Thomas J. .

TETRAHEDRON LETTERS, 2006, 47 (36) :6425-6427

[2] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[3] N-H carbazole synthesis from 2-chloroanilines via consecutive amination and C-H activation [J].

Bedford, Robin B. ;

Betham, Michael .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (25) :9403-9410

[4] SYNTHESIS OF CARBAZOLE ALKALOIDS [J].

BERGMAN, J ;

PELCMAN, B .

PURE AND APPLIED CHEMISTRY, 1990, 62 (10) :1967-1976

[5]

Bringmann G, 1998, SYNTHESIS-STUTTGART, P1501

[6] Structure and optical properties of 2,3,7,9-polysubstituted carbazole derivatives.: Experimental and theoretical studies [J].

Díaz, JL ;

Dobarro, A ;

Villacampa, B ;

Velasco, D .

CHEMISTRY OF MATERIALS, 2001, 13 (08) :2528-2536

[7]

Gilchrist T. L., 1985, HETEROCYCLIC CHEM

[8] Carbazole-containing polymers: synthesis, properties and applications [J].

Grazulevicius, JV ;

Strohriegl, P ;

Pielichowski, J ;

Pielichowski, K .

PROGRESS IN POLYMER SCIENCE, 2003, 28 (09) :1297-1353

[9] Cell apoptosis induced by a synthetic carbazole compound LCY-2-CHO is mediated through activation of caspase and mitochondrial pathways [J].

Hsu, MJ ;

Chao, Y ;

Chang, YH ;

Ho, FM ;

Huang, LJ ;

Huang, YL ;

Luh, TY ;

Chen, CP ;

Lin, WW .

BIOCHEMICAL PHARMACOLOGY, 2005, 70 (01) :102-112

[10] Occurrence, biological activity, and convergent organometallic synthesis of carbazole alkaloids [J].

Knölker, HJ .

NATURAL PRODUCTS SYNTHESIS II TARGETS, METHODS, CONCEPTS, 2005, 244 :115-148

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