Synthesis of highly functionalized β-lactam substituted pyrroloisoquinoline and indolizinoindole system by sequential intermolecular 1,3-dipolar cycloaddition reaction and Pictet-Spengler cyclization

被引：21

作者：

Arumugam, Natarajan ^{[1
]}

Raghunathan, Raghavachary ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2010年 / 66卷 / 04期

关键词：

1,3-Dipolar cycloaddition; beta-Lactam; Pyrroloisoquinoline; Indolizinoindole; Pictet-Spengler cyclization; 2-AZETIDINONE-TETHERED AZOMETHINE YLIDES; BAYLIS-HILLMAN ADDUCTS; STEREOSELECTIVE-SYNTHESIS; STEREOCONTROLLED SYNTHESIS; PYRROLIZIDINE SYSTEMS; METHYL; ESTERS; ETHYL; ORGANOCATALYSIS; CONVERSION;

D O I：

10.1016/j.tet.2009.11.085

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of novel pyrroloisoquinoline and indolizinoindole derivatives with beta-lactam unit has been achieved by sequential intermolecular 1,3-dipolar cycloaddition reaction and Pictet-Spengler cyclization. The azomethine ylide derived from beta-lactam imine of alpha-amino ester in the presence of silver acetate reacted with nitrostyrenes to give pyrrolidinyl beta-lactam, which underwent Pictet-Spengler cyclization in presence of trifluoroacetic acid to give pyrroloisoquinolines and indolizinoindoles. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：969 / 975

页数：7

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