SYNTHESIS OF NOVEL SPIROHETEROCYCLES THROUGH 1,3-DIPOLAR CYCLOADDITION OF AZOMETHINE YLIDES WITH TRIARYLIDENEACETYLACETONE THROUGH DECARBOXYLATION

被引：7

作者：

Murugan, Ramalingam ^{[2
]}

Raghunathan, R. ^{[3
]}

Narayanan, S. Sriman ^{[1
]}

机构：

[1] Univ Madras, Dept Analyt Chem, Madras 600025, Tamil Nadu, India

[2] Orchid Res Labs Ltd, Dept Med Chem, Madras, Tamil Nadu, India

[3] Univ Madras, Dept Organ Chem, Chennai, Tamil Nadu, India

来源：

SYNTHETIC COMMUNICATIONS | 2010年 / 40卷 / 21期

关键词：

Azomethine ylide; 1; 3-dipolar cycloaddition; spiropyrrolidine; spiropyrrolizine; triarylideneacetylacetone; ASYMMETRIC TOTAL-SYNTHESIS; IMINIUM ION ROUTE; X=Y-ZH COMPOUNDS; POTENTIAL 1,3-DIPOLES; PENTACYCLIC INTERMEDIATE; NITRILE OXIDES; DERIVATIVES; ALKALOIDS; OXINDOLE; CONCISE;

D O I：

10.1080/00397910903341189

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Triarylideneacetylacetone undergoes regioselective 1,3-dipolar cycloaddition reactions with azomethine ylide derived from isatin and L-proline/sarcosine/octahydro-1H-indole-2-carboxylic acid by decarboxylation, affording a series of spiroheterocycles. This one-pot, three-component tandem reaction is efficient and yields novel spiroheterocylic compounds in good yields. The structure and stereochemistry of the cycloadduct have been established by single-crystal x-ray and spectroscopic techniques.

引用

页码：3135 / 3151

页数：17

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