Orthogonal synthesis of indolines and isoquinolines via aryne annulation

被引：222

作者：

Gilmore, Christopher D. ^{[1
]}

Allan, Kevin M. ^{[1
]}

Stoltz, Brian M. ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 05期

关键词：

D O I：

10.1021/ja0780582

中图分类号：

O6 [化学];

学科分类号：

0703 [化学];

摘要：

Described in this report is the development of two unique methodologies exploiting the reactivity of arynes. Reaction of N-carbamoyl-functionalized enamine derivatives with benzyne affords substituted indolines. An orthogonal reactivity is uncovered when related enamine derivatives are modified as amides, such that isoquinolines are formed as the product of condensation with benzyne. This latter transformation is applied to a concise total synthesis of the opiale alkaloid papaverine.

引用

页码：1558 / +

页数：3

共 49 条

[1]

Structure of 'diphenylene' [J].

Baker, W .

NATURE, 1942, 150 :210-211

[2]

Reaction of benzyne with styrene oxide:: Insertion of arynes into a C-O bond of epoxides [J].

Beltran-Rodil, Sandra ;

Pena, Diego ;

Guitian, Enrique .

SYNLETT, 2007, (08) :1308-1310

[3]

Bentley K.W., 1998, The Isoquinoline Alkaloids, P107

[4]

β-Phenylethylamines and the isoquinoline alkaloids [J].

Bentley, KW .

NATURAL PRODUCT REPORTS, 2005, 22 (02) :249-268

[5]

BEVIS MG, 1887, TETRAHEDRON, V25, P1585

[6]

REACTION OF 4-BROMO-1,2-DIMETHYLBENZENE WITH VARIOUS NUCLEOPHILES VIA ARYNE REACTION [J].

BIEHL, ER ;

RAZZUK, A ;

JOVANOVIC, MV ;

KHANAPURE, SP .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5157-5160

[7]

Bischler A., 1893, CHEM BER-RECL, V26, P1903, DOI [DOI 10.1002/CBER.189302602143, 10.1002/cber.189302602143]

[8]

CYCLOADDITIONS OF BENZYNE WITH CYCLIC OLEFINS - COMPETITION BETWEEN 2 + 4, ENE, AND 2 + 2 REACTION PATHWAYS [J].

CREWS, P ;

BEARD, J .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (03) :522-528

[9]

DELMAZZA D, 1981, J CHEM SOC CHEM COMM, P124

[10]

Dobner O., 1887, LIEBIGS ANN CHEM, V242, P265, DOI DOI 10.1002/JLAC.18872420302

← 1 2 3 4 5 →