Microwave-Promoted Synthesis of N-Heterocycles by Tandem Imination/Annulation of γ- and δ-Ketoalkynes in the Presence of Ammonia

被引：78

作者：

Alfonsi, Maria ^{[2
]}

Dell'Acqua, Monica ^{[1
]}

Facoetti, Diego ^{[1
]}

Arcadi, Antonio ^{[2
]}

Abbiati, Giorgio ^{[1
]}

Rossi, Elisabetta ^{[1
]}

机构：

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

[2] Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Laquila, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 17期

关键词：

Alkynes; Heterocycles; Domino reactions; Microwaves; Titanium; CATALYZED CARBONYLATIVE CYCLIZATION; ONE-POT REACTION; 3-COMPONENT REACTION; EFFICIENT ROUTE; DIELS-ALDER; 3-SUBSTITUTED; 4-AROYLISOQUINOLINES; 3,4-DISUBSTITUTED ISOQUINOLINES; INTRAMOLECULAR CYCLIZATION; ELECTROPHILIC CYCLIZATION; NUCLEOPHILIC-ADDITION;

D O I：

10.1002/ejoc.200900014

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

The synthesis of 3-substituted 1-methylpyrrolo[1,2-a]pyrazines and 3-substituted isoquinolines was achieved by the intramolecular cyclisation of 2-acetyl-1-propargylpyrroles and 2-alkynylbenzaldehydes, respectively, in the presence of ammonia under microwave heating. The tandem imination/annulation of 2-alkynylbenzaldehydes was easily accomplished under standard conditions, while TiCl4 was used to achieve pyrrolo[1,2-a]pyrazines. The reaction mechanism and the regioselectivity were discussed on the basis of theoretical calculations and spectroscopic data. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：2852 / 2862

页数：11

共 78 条

[1]

Synthesis of 3,3′-disubstituted-2,2′-biindolyls through sequential palladium-catalysed reactions of 2,2,2-trifluoro-N-(2-(4-[2,2,2-trifluoro-acetylamino)-phenyl]-buta-1,3-diynyl)-phenyl)-acetamide with organic halides/triflates [J].

Abbiati, G ;

Arcadi, A ;

Beccalli, E ;

Bianchi, G ;

Marinelli, F ;

Rossi, E .

TETRAHEDRON, 2006, 62 (13) :3033-3039

[2]

Domino addition/annulation of δ-alkynylaldehydes and oxygen nucleophiles:: a new entry to [1,4]oxazino[4,3-a]indoles [J].

Abbiati, G ;

Canevari, V ;

Caimi, S ;

Rossi, E .

TETRAHEDRON LETTERS, 2005, 46 (42) :7117-7120

[3]

Palladium-assisted multicomponent synthesis of 2-aryl-4-aminoquinolines and 2-aryl-4-amino[1,8]naphthyridines [J].

Abbiati, G ;

Arcadi, A ;

Canevari, V ;

Capezzuto, L ;

Rossi, E .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6454-6460

[4]

Intramolecular cyclization of δ-iminoacetylenes:: A new entry to pyrazino[1,2-a]indoles [J].

Abbiati, G ;

Arcadi, A ;

Bellinazzi, A ;

Beccalli, E ;

Rossi, E ;

Zanzola, S .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :4088-4095

[5]

Novel intramolecular cyclization of N-alkynyl heterocycles containing proximate nucleophiles [J].

Abbiati, G ;

Arcadi, A ;

Beccalli, E ;

Rossi, E .

TETRAHEDRON LETTERS, 2003, 44 (28) :5331-5334

[6]

Abbiati G, 2001, SYNTHESIS-STUTTGART, P2477

[7]

Palladium catalyzed synthesis of 4-substituted-2-phenylimidazoles from N-propargyl-benzamidine [J].

Abbiati, Giorgio ;

Arcadi, Antonio ;

Canevaria, Valentina ;

Rossia, Elisabetta .

TETRAHEDRON LETTERS, 2007, 48 (48) :8491-8495

[8]

Rh-catalyzed sequential hydroarylation/hydrovinylation-heterocyclization of β-(2-aminophenyl)-α,β-ynones with organoboron derivatives:: A new approach to functionalized quinolines [J].

Abbiati, Giorgio ;

Arcadi, Antonio ;

Marinelli, Fabio ;

Rossi, Ellsabetta ;

Verdecchia, Mirella .

SYNLETT, 2006, (19) :3218-3224

[9]

TiCl4/t-BuNH2-promoted hydroamination/annulation of δ-keto-acetylenes:: Synthesis of novel pyrrolo[1,2-a]indol-2-carbaldehydes [J].

Abbiati, Giorgio ;

Casoni, Alessandro ;

Canevari, Valentina ;

Nava, Donatella ;

Rossi, Elisabetta .

ORGANIC LETTERS, 2006, 8 (21) :4839-4842

[10]

TiCl4-catalyzed intermolecular hydroamination reactions [J].

Ackermann, L .

ORGANOMETALLICS, 2003, 22 (22) :4367-4368

← 1 2 3 4 5 6 7 8 →