N,N-disubstituted propargylamines as tools in the sequential 1,3-dipolar cycloaddition/arylation processes to the formation of polyheterocyclic systems

被引：29

作者：

Basolo, Luca ^{[1
]}

Beccalli, Egle M. ^{[1
]}

Borsini, Elena ^{[2
]}

Broggini, Gianluigi ^{[2
]}

Pellegrino, Sara ^{[1
]}

机构：

[1] Univ Milan, Fac Farm, Ist Chim Organ A Marchesini, I-20133 Milan, Italy

[2] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy

来源：

TETRAHEDRON | 2008年 / 64卷 / 35期

关键词：

D O I：

10.1016/j.tet.2008.06.042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting from N,N-disubstituted propargylamines, through a one-pot sequential 1,3-dipolar cycloaddition/Pd-catalyzed arylation, polyheterocyclic systems were obtained in only one step. The outcome of the cycloadditions, performed with 1,3-dipoles nitriloxide and azide, was totally regioselective. The subsequent Pd-catalyzed arylation achieved using ligand-free conditions involved the unsubstituted carbon of the heterocyclic ring. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：8182 / 8187

页数：6

共 32 条

[1] Pd-catalyzed cyclization of 1-allyl-2-indolecarboxamides by intramolecular amidation of unactivated ethylenic bond [J].

Abbiati, G ;

Beccalli, E ;

Broggini, G ;

Martinelli, M ;

Paladino, G .

SYNLETT, 2006, (01) :73-76

[2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[3] Microwave-assisted intramolecular cyclization of electron-rich heterocycle derivatives by a palladium-catalyzed coupling reaction [J].

Beccalli, Egle M. ;

Broggini, Glanluig ;

Martinelli, Michela ;

Sottocornolab, Silvia .

SYNTHESIS-STUTTGART, 2008, 1 (01) :136-140

[4] New 4-spiroannulated tetrahydroisoquinolines by a one-pot sequential procedure.: Isolation and characterization of σ-alkylpalladium Heck intermediates [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Martinelli, Michela ;

Masciocchi, Norberto ;

Sottocornola, Silvia .

ORGANIC LETTERS, 2006, 8 (20) :4521-4524

[5] Practical and efficient palladium-promoted synthesis of indole systems containing medium- and large-ring-fused heterocycles [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Martinelli, Michela ;

Paladino, Giuseppe ;

Rossi, Elisabetta .

SYNTHESIS-STUTTGART, 2006, 14 (14) :2404-2412

[6] Synthesis of tricyclic quinolones and naphthyridones by intramolecular heck cyclization of functionalized electron-rich heterocycles [J].

Beccalli, EM ;

Broggini, G ;

Martinelli, M ;

Paladino, G ;

Zoni, C .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (10) :2091-2096

[7] Regioselective formation of six- and seven-membered ring by intramolecular Pd-catalyzed amination of N-allyl-anthranilamides [J].

Beccalli, EM ;

Broggini, G ;

Paladino, G ;

Penoni, A ;

Zoni, C .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5627-5630

[8] Efficient and practical synthesis of 4(5)-Aryl-1H-imidazoles and 2,4(5)-Diaryl-1H-imidazoles via highly selective palladium-catalyzed arylation reactions [J].

Bellina, Fabio ;

Cauteruccio, Silvia ;

Rossi, Renzo .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8543-8546

[9]

Bonjouklian R., 2001, Int. Patent Appl. Pub., Patent No. 2001046199

[10]

BONJOUKLIAN R, 2001, Patent No. 2001027116

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