Synthesis of 7H-Indolo[2,3-c]quinolines by Chemoselective Suzuki Reaction Followed by a Ring-Closing Two-Fold Buchwald-Hartwig Reaction of 3-Bromo-4-iodoquinoline

被引：7

作者：

Rivera, Rodisnel Perdomo ^{[1
,3
]}

Ehlers, Peter ^{[1
,2
]}

Rodriguez, Eugenio Torres ^{[3
]}

Langer, Peter ^{[1
,2
]}

机构：

[1] Univ Rostock, Inst Chem, A Einstein Str 3, D-18059 Rostock, Germany

[2] Univ Rostock, Leibniz Inst Katalyse eV, A Einstein Str 29a, D-18059 Rostock, Germany

[3] Univ Granma, Study Ctr Appl Chem, Carretera Manzanillo Km 1712, Bayamo 85100, Granma, Cuba

来源：

CHEMISTRYSELECT | 2018年 / 3卷 / 40期

关键词：

Chemoselectivity; Cross-coupling reactions; Heterocycles; Palladium; DOUBLE N-ARYLATION; CRYPTOLEPIS-SANGUINOLENTA; INDOLOQUINOLINE ALKALOIDS; ANTIPLASMODIAL ACTIVITY; ANTIMALARIAL ACTIVITY; CONVENIENT SYNTHESIS; PRIMARY AMINES; IN-VITRO; ISOCRYPTOLEPINE; DERIVATIVES;

D O I：

10.1002/slct.201802320

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-functionalized 7H-indolo[2,3-c]quinolines have been synthesized by chemoselective Suzuki-reaction followed by a ring-closing two-fold Buchwald-Hartwig reaction. The developed methodology allows the application of various anilines, benzyl amines as well as aliphatic amines and led to corresponding products in high yields.

引用

页码：11177 / 11179

页数：3

共 32 条

[1] Ablordeppey S. Y., 2012, US, Patent No. [2012/ 0165369, 20120165369]
[2] New Route to the Synthesis of the Isocryptolepine Alkaloid and Its Related Skeletons Using a Modified Pictet-Spengler Reaction
Agarwal, Piyush K.
Sawant, Devesh
Sharma, Sunil
Kundu, Bijoy
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (02) : 292 - 303
[3] Synthesis of quinolines, 2-quinolones, phenanthridines, and 6(5H)-phenanthridinones via palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitroarenes with β-halo-enals, -enones, or -esters
Banwell, MG
Lupton, DW
Ma, XH
Renner, J
Sydnes, MO
[J]. ORGANIC LETTERS, 2004, 6 (16) : 2741 - 2744
[4] A concise synthesis of indoloquinoline skeletons applying two consecutive Pd-catalyzed reactions
Boganyi, Borbala
Kaman, Judit
[J]. TETRAHEDRON, 2013, 69 (45) : 9512 - 9519
[5] Byun J. H., 2011, Patent: KR, Patent No. 2011105269
[6] Aplidiopsamine A, an Antiplasmodial Alkaloid from the Temperate Australian Ascidian, Aplidiopsis confluata
Carroll, Anthony R.
Duffy, Sandra
Avery, Vicky M.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (23) : 8291 - 8294
[7] Cho H. J., 2015, Patent: KR, Patent No. 2015052705
[8] New alkaloids from Cryptolepis sanguinolenta
Cimanga, K
DeBruyne, T
Pieters, L
Claeys, M
Vlietinck, A
[J]. TETRAHEDRON LETTERS, 1996, 37 (10) : 1703 - 1706
[9] In vitro and in vivo antiplasmodial activity of cryptolepine and related alkaloids from Cryptolepis sanguinolenta
Cimanga, K
DeBruyne, T
Pieters, L
Vlietinck, AJ
[J]. JOURNAL OF NATURAL PRODUCTS, 1997, 60 (07): : 688 - 691
[10] THE TOTAL SYNTHESIS OF CYSTODYTINS
CIUFOLINI, MA
BYRNE, NE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) : 8016 - 8024

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