Aza-annulation of polarized N,S- and N,N-ketene acetals with itaconic anhydride: Synthesis of novel functionalized 1,2,3,4-tetrahydro-2-pyridones and related azabicycles

被引：51

作者：

Chakrabarti, S

Panda, K

Misra, NC

Ila, H ^{[1
]}

Junjappa, H

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

[2] BioOrgan Appl Mat Pvt Ltd, Bangalore 560058, Karnataka, India

来源：

SYNLETT | 2005年 / 09期

关键词：

alkaloids; annulation; esters; heterocycles; lactams; Michael addition; nitriles;

D O I：

10.1055/s-2005-868491

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of novel highly functionalized 2-oxo-(1,2,3,4-tetrahydropyridin-3-yl) acetic acids has been described via aza-annulation of both acyclic and cyclic alpha-oxo- and alpha-nitro-N,S-and-N,N-ketene acetals with itaconic anhydride.

引用

页码：1437 / 1441

页数：5

共 51 条

[1] Synthesis of enantiopure cis- and trans-2,3-disubstituted piperidines [J].

Agami, C ;

Dechoux, L ;

Ménard, C ;

Hebbe, S .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7573-7576

[2] Enantioselective synthesis of conformationally restricted analogs of NMDA: cis- and trans-piperidine-2,3-dicarboxylic acids and methylated derivatives [J].

Agami, C ;

Hamon, L ;

KadouriPuchot, C ;

LeGuen, V .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) :5736-5742

[3]

AGGARWAL V, 1982, SYNTHESIS-STUTTGART, P65

[4]

AGGARWAL V, 1983, SYNTHESIS-STUTTGART, P147

[5] THE ASYMMETRIC MICHAEL REACTION USING CHIRAL IMINES UNDER NEUTRAL CONDITIONS - STEREOCHEMICAL EVIDENCES IN SUPPORT OF A CYCLIC TRANSITION-STATE [J].

AMBROISE, L ;

DESMAELE, D ;

MAHUTEAU, J ;

DANGELO, J .

TETRAHEDRON LETTERS, 1994, 35 (52) :9705-9708

[6]

Balasubramanian M., 1996, COMPREHENSIVE HETERO, V5, P245, DOI 10.1016/B978-008096518-5.00109

[7] ASYMMETRIC FORMATION OF QUATERNARY CENTERS THROUGH AZA-ANNULATION OF CHIRAL BETA-ENAMINO ESTERS WITH ACRYLATE DERIVATIVES [J].

BARTA, NS ;

BRODE, A ;

STILLE, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) :6201-6206

[8] A facile access to 2-methylthio/alkoxy/amino-3-acylimidazo[1,2-a]pyridines based on cupric chloride promoted oxidative ring closure of α-oxoketene N,S-, N,O-, and N,N-acetals [J].

Barun, HO ;

Ila, H ;

Junjappa, H ;

Singh, OM .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) :1583-1587

[9] Ring annulation with tetrahydroisoquinoline-derived enaminones:: Highly convergent routes to functionalized pyrrolo[2,1-a]- and indolo[2,1-a]isoquinolines [J].

Barun, O ;

Chakrabarti, S ;

Ila, H ;

Junjappa, H .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) :4457-4461

[10]

Barun O, 2000, SYNLETT, P653

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