Synthesis of α-Carbolines Starting from 2,3-Dichloropyridines and Substituted Anilines

被引：74

作者：

Hostyn, Steven ^{[1
]}

Van Baelen, Gitte ^{[1
]}

Lemiere, Guy L. F. ^{[1
]}

Maes, Bert U. W. ^{[1
]}

机构：

[1] Univ Antwerp, Dept Chem, B-2020 Antwerp, Belgium

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 16期

关键词：

alpha-carbolines; C-H activation; direct arylation; malaria; microwave heating; palladium;

D O I：

10.1002/adsc.200800077

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

9H-alpha-Carbolines have been prepared via consecutive intermolecular Buchwald-Hartwig reaction and Pd-catalyzed intramolecular direct arylation from commercially available 2,3-dichloropyridines and substituted anilines. The combination of a high reaction temperature (180 degrees C) and the use of DBU were found to be crucial for the intramolecular direct arylation reactions of the 3-cliloro-N-phenylpyridin-2-amines as no reaction was observed at 120 degrees C and 180 degrees C using different inorganic and other organic bases. On the other hand, nitrogenmethylated pyridine analogues of these substrates {N-[3-chloro-l-methylpyridin-2(1H)-ylidene]anilines} do undergo ring closure at 120 degrees C, with K3PO4 as base, affording the respective 1-methyl-1H-alpha-carbolines in good yields.

引用

收藏

页码：2653 / 2660

页数：8

相关论文

共 72 条

[41] Auto-tandem catalysis:: Synthesis of substituted 11H-indolo [3,2-c]quinolines via palladium-catalyzed intermolecular C-N and intramolecular C-C bond formation [J].

Meyers, Caroline ;

Rornbouts, Geert ;

Loones, Kristof T. J. ;

Coelho, Alberto ;

Maes, Bert U. W. .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (03) :465-470

[42]

Molina P, 1999, SYNTHESIS-STUTTGART, P326

[43] Investigative studies on the formation of the imidazo [4′,5′:3,4]pyrido[2,3-b]indole ring:: Formal synthesis of the alkaloids grossularines-1 and 2.: X-ray crystal structures of 5-indol-3-yl-imidazole and bisimidazocarbazole derivatives. [J].

Molina, P ;

Fresneda, PM ;

Sanz, MA ;

Foces-Foces, C ;

de Arellano, MCR .

TETRAHEDRON, 1998, 54 (33) :9623-9638

[44] Practical palladium catalysts for C-N and C-O bond formation [J].

Muci, AR ;

Buchwald, SL .

CROSS-COUPLING REACTIONS: A PRACTICAL GUIDE, 2002, 219 :131-209

[45] 7-AZAINDOLE .5. INVESTIGATIONS OF ALTERNATIVE SYNTHESES OF THE RING SYSTEM [J].

OKUDA, S ;

ROBISON, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (03) :740-743

[46] Synthesis of α-carbolines from β-(3-Indolyl) ketone O-2,4-dinitrophenyloximes [J].

Ono, A ;

Narasaka, K .

CHEMISTRY LETTERS, 2001, (02) :146-147

[47] Double reductive cyclization: a facile synthesis of the indoloquinoline alkaloid cryptotackieine [J].

Parvatkar, P. T. ;

Parameswaran, P. S. ;

Tilve, S. G. .

TETRAHEDRON LETTERS, 2007, 48 (44) :7870-7872

[48]

PECZYNSKACZOCH W, 1986, ARCH IMMUNOL THER EX, V34, P327

[49] First Suzuki-Miyaura type cross-coupling of ortho-azidobromobenzene with arylboronic acids and its application to the synthesis of fused aromatic indole-heterocycles [J].

Pudlo, Marc ;

Csanyi, Dorottya ;

Moreau, Fabien ;

Hajos, Gyorgy ;

Riedl, Zsuzsanna ;

Sapi, Janos .

TETRAHEDRON, 2007, 63 (41) :10320-10329

[50] Synthesis of novel 1-methyl-1H-pyridazino[3,4-b]indoles [J].

Riedl, Z ;

Monsieurs, K ;

Krajsovszky, G ;

Dunkel, P ;

Maes, BUW ;

Tapolcsányi, P ;

Egyed, O ;

Boros, S ;

Mátyus, P ;

Pieters, L ;

Lemière, GLF ;

Hajós, G .

TETRAHEDRON, 2006, 62 (01) :121-129

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