Facile Stereoselective Synthesis and Structural Study of Camphor- and Fenchone-Based Spirocyclic 1,3,4-Oxadiazolines

被引：3
|
作者：
Kovaleva, Kseniya S. [1 ]
Abdrakhmanova, Veronika S. [1 ]
Yarovaya, Olga I. [1 ]
Gatilov, Yuriy V. [1 ]
Rybalova, Tatyana V. [1 ]
Salakhutdinov, Nariman F. [1 ]
机构：
[1] NN Vorozhtsov Novosibirsk Inst Organ Chem, Dept Med Chem, Lab Physiol Act Cpds, Lavrentyev Ave 9, Novosibirsk 630090, Russia
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 42期
关键词：
spirocyclic compounds; 1,3,4-oxadiazolines; monoterpene; intramolecular cyclization; isomerization; DERIVATIVES; INHIBITORS; IMINES;
D O I：
10.1002/ejoc.202300811
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
For the first time, an effective method for the synthesis of spirocyclic camphor- and fenchone-based 1,3,4-oxadiazolines has been developed. The influence of the molecular structure of the terpene substrate on the reaction stereoselectivity was studied. The structural features of the target products were studied using NMR spectroscopy and X-ray diffraction analysis. The proposed method allows obtaining of spirocyclic products with a wide structural diversity, stereoselectively and in good yields. For the first time, an effective method for the synthesis of spirocyclic camphor- and fenchone-based 1,3,4-oxadiazolines has been developed. The influence of the terpene scaffold on the reaction stereoselectivity was studied. The proposed method allows obtaining of spirocyclic products with a wide structural diversity, stereoselectively and in good yields.image
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页数：6
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