Organocatalytic Diastereoselective Synthesis of Spiro[3-azabicyclo[3.1.0]hexanes] via 1,3-Dipolar Cycloaddition of Azomethine Ylides with Cyclopropenes

被引：2

作者：

Pronina, Yu. A. ^{[1
]}

Viktorov, N. B. ^{[1
]}

Selivanov, S. I. ^{[1
,2
]}

Kornev, A. A. ^{[3
]}

Ponyaev, A. I. ^{[1
]}

Boitsov, V. M. ^{[3
]}

Stepakov, A. V. ^{[1
,3
,4
]}

机构：

[1] Techn Univ, St Petersburg State Inst Technol, St Petersburg 190013, Russia

[2] St Petersburg State Univ, Lab Biomol NMR, St Petersburg 199034, Russia

[3] lferov Acad Univ, St Petersburg 194021, Russia

[4] St Petersburg State Univ, St Petersburg 199034, Russia

来源：

RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2024年 / 94卷 / 04期

关键词：

1,3-dipolar cycloaddition; 3-azabicyclo[3.1.0]hexanes; azomethine ylides; cyclopropenes; isatins; acenaphthenequinone; squaramides; organocatalysis; ENANTIOSELECTIVE SYNTHESIS; ONE-POT; DISCOVERY; REGIOSELECTIVITY; ACCESS;

D O I：

10.1134/S107036322404008X

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A three-component organocatalytic reaction of 1,3-dipolar cycloaddition between the in situ generated azomethine ylides and 3-substituted 1,2-diphenylcyclopropenes is described. The azomethine ylides have been generated via condensation of aromatic compounds (such as isatins and acenaphthenequinone) with benzylamines. The reaction has afforded derivatives of 3-azabicyclo[3.1.0]hexane, spiro-fused with the fragments of 2-oxindole and acenaphthylene-1(2H)-one. The cycloadducts have been obtained with yield up to 91%, mainly as individual diastereomers. The influence of bifunctional squaramide-based organocatalysts on the course of these three-component reactions has been investigated. Antiproliferative activity of selected synthesized compounds with respect to the human erythromyelosis (K562) and melanoma (Sk-mel-2) cell lines has been assessed in vitro by means of MTS analysis.

引用

页码：804 / 823

页数：20

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