A Highly Stereocontrolled Intramolecular Cycloaddition Reaction of Azomethine Ylide Activated by a Pyrimidine Ring: Access to Novel Tricyclic Hexahydro-1H-pyrrolo[2′,3′:4,5]pyrido[2,3-d]pyrimidines

被引：9

作者：

Xie, Hongxiang

Xiang, Jinbao

Dang, Qun ^{[1
]}

Bai, Xu

机构：

[1] Jilin Univ, Coll Chem, Ctr Combinatorial Chem & Drug Discovery, Changchun 130021, Jilin, Peoples R China

来源：

SYNLETT | 2012年 / 04期

关键词：

azomethine ylide; intramolecular cycloaddition; 1,3-dipolar cycloaddition; pyrimidine; pyrrolidine; IMINIUM ION ROUTE; X=Y-ZH COMPOUNDS; 1,3-DIPOLAR CYCLOADDITION; DIPOLAR CYCLOADDITION; POTENTIAL 1,3-DIPOLES; CONSTRUCTION; ALDEHYDES; RECEPTOR; AMINES;

D O I：

10.1055/s-0031-1290333

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A pyrimidine ring was discovered to aid formation of an azomethine ylide undergoing intramolecular cycloaddition reactions. This method enabled efficient synthesis of a novel tricyclic pyrimidine-piperidine-pyrrolidine scaffold from various pyrimidinemethyl amines and aldehydes in complete stereocontrol and could be rationalized by an S-shaped azomethine ylide intermediate.

引用

页码：585 / 588

页数：4

共 39 条

[1] Novel dipolarophiles and dipoles in the metal-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides [J].

Adrio, Javier ;

Carretero, Juan C. .

CHEMICAL COMMUNICATIONS, 2011, 47 (24) :6784-6794

[2] Silver-mediated synthesis of heterocycles [J].

Alvarez-Corral, Miriam ;

Munoz-Dorado, Manuel ;

Rodirguez-Garcia, Ignacio .

CHEMICAL REVIEWS, 2008, 108 (08) :3174-3198

[3] X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .29. THE IMINIUM ION ROUTE TO AZOMETHINE YLIDES - REACTION OF CYCLIC SECONDARY-AMINES WITH MONO-FUNCTIONAL AND BI-FUNCTIONAL ALDEHYDES [J].

ARDILL, H ;

FONTAINE, XLR ;

GRIGG, R ;

HENDERSON, D ;

MONTGOMERY, J ;

SRIDHARAN, V ;

SURENDRAKUMAR, S .

TETRAHEDRON, 1990, 46 (18) :6449-6466

[4] Novel Regio- and Stereoselective Synthesis of Functionalized 3-Spiropyrrolidines and 3-Spiropyrrolizidines Using the Baylis-Hillman Adducts Derived from Nitroolefins [J].

Bakthadoss, Manickam ;

Sivakumar, Nagappan .

SYNLETT, 2009, (06) :1014-1018

[5] Highly Diastereoselective Synthesis of Substituted Pyrrolidines Using a Sequence of Azomethine Ylide Cycloaddition and Nucleophilic Cyclization [J].

Belanger, Guillaume ;

Darsigny, Veronique ;

Dore, Michael ;

Levesque, Francois .

ORGANIC LETTERS, 2010, 12 (07) :1396-1399

[6] Synthesis of the core ring system of the stemona alkaloids by cascade condensation, cyclization, intramolecular cycloaddition [J].

Burrell, Adam. J. M. ;

Watson, Luke ;

Martin, Nathaniel G. ;

Oram, Niall ;

Coldham, Iain .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) :4530-4532

[7]

Burrell AJM, 2010, CURR ORG SYNTH, V7, P312

[8] Stereoselective Formation of Fused Tricyclic Amines from Acyclic Aldehydes by a Cascade Process Involving Condensation, Cyclization, and Dipolar Cycloaddition [J].

Burrell, Adam J. M. ;

Coldham, Iain ;

Watson, Luke ;

Oram, Niall ;

Pilgram, Christopher D. ;

Martin, Nathaniel G. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (06) :2290-2300

[9] Intramolecular dipolar cycloaddition reactions of azomethine ylides [J].

Coldham, I ;

Hufton, R .

CHEMICAL REVIEWS, 2005, 105 (07) :2765-2809

[10] Cascade Cyclization, Dipolar Cycloaddition to Bridged Tricyclic Amines Related to the Daphniphyllum Alkaloids [J].

Coldham, Iain ;

Burrell, Adam J. M. ;

Guerrand, Helene D. S. ;

Oram, Niall .

ORGANIC LETTERS, 2011, 13 (06) :1267-1269

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