一种通过硝酮1,3-环加成偶极反应合成三环化合物的新方法。

A New Way to the Synthesis of Tricyclic Compounds via Nitrone 1,3- cycloaddition Dipolar Reaction.

作者信息

Zga Nadia, Azouz Mounir, Bouchouk Djamel

机构信息

Laboratory of Aquatic and Terrestrial Ecosystems, Organic and Bioorganic Chemistry Group, University of Mohamed- Cherif Messaadia, Souk Ahras, 41000, Algeria.

出版信息

Curr Org Synth. 2023;20(5):560-575. doi: 10.2174/1570179419666220825125900.

DOI:10.2174/1570179419666220825125900

PMID:36028960

Abstract

OBJECTIVE

This study aimed at developing new methodologies for 1,3-dipolar cycloaddition.

METHODS

A new series of tricyclic derivatives (13a-d) were synthesized via 1, 3-dipolar cycloaddition of nitrones (8a-c) and (9a-c) using intramolecular cyclisation at the reflux of toluene and radical intramolecular cyclisation in the presence of tributyltin hydride and AIBN as an initiator in benzene, which are two techniques to prepare cycloadducts (11a-d), followed by cleavage of the N-O bond performed using Sml in THF.

RESULTS

The structures of these new tricyclic derivatives have been confirmed by Mass, 1H-NMR (1d, 2d), 13C-NMR, and IR spectral data.

CONCLUSION

In summary, we have investigated the possibility of synthesizing some new and straightforward methods to access an A-C-D tricyclic skeleton of morphinans from symmetrical arylcyclohexadienes.

摘要

目的

本研究旨在开发1,3 - 偶极环加成的新方法。

方法

通过硝酮（8a - c）和（9a - c）的1,3 - 偶极环加成反应，采用两种技术合成了一系列新的三环衍生物（13a - d）。一种技术是在甲苯回流条件下进行分子内环化反应，另一种是在苯中以三丁基氢化锡和偶氮二异丁腈作为引发剂进行自由基分子内环化反应，从而制备环加成物（11a - d），随后在四氢呋喃中使用钐（II）碘化物进行N - O键的裂解。