A concise synthesis of indoloquinoline skeletons applying two consecutive Pd-catalyzed reactions

被引：62

作者：

Boganyi, Borbala ^{[1
,2
]}

Kaman, Judit ^{[1
]}

机构：

[1] BioBlocks Magyarorszag Kft, H-1045 Budapest, Hungary

[2] Eotvos Lorand Univ, Inst Chem, Budapest, Hungary

来源：

TETRAHEDRON | 2013年 / 69卷 / 45期

关键词：

Indoloquinoline; Dihaloquinoline; Buchwald-Hartwig amination; Heck-type reaction; Regioselectivity; Microwave; CONVENIENT SYNTHESIS; HALOGEN EXCHANGE; ARYLATION; ISOCRYPTOLEPINE; QUINOLINES; CRYPTOSANGUINOLENTINE; 4(1H)-QUINOLONES; CRYPTOTACKIEINE; REARRANGEMENT; CRYPTOLEPINE;

D O I：

10.1016/j.tet.2013.08.019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The indoloquinoline alkaloids cryptolepine (1), neocryptolepine (2), isocryptolepine (3), and isoneocryptolepine (4) are important tools in traditional medicine. Now, their precursors 1a-4a were synthesized in two steps starting from the corresponding bromo-iodoquinolines. Our strategy is based on palladium-catalyzed reactions, applying regioselective Buchwald-Hartwig amination on 2,3- and 3,4-dihaloquinolines followed by an intramolecular Heck-type reaction. Both steps were carried out under microwave irradiation. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

引用

页码：9512 / 9519

页数：8

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