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环己-3-烯-1-甲酰胺衍生物中的异常重排：通往双环内酯的途径。

Unusual Rearrangements in Cyclohex-3-ene-1-carboxamide Derivatives: Pathway to Bicyclic Lactones.

作者信息

Gundogdu Ozlem, Aytaç Sertan, Şahin Ertan, Kara Yunus

机构信息

Department of Food Technology, Kaman Vocational School, Ahi Evran University, Kirsehir 40100, Turkey.

Department of Chemistry, Faculty of Science, Atatürk University, Erzurum 25240, Turkey.

出版信息

ACS Omega. 2024 May 14;9(21):22970-22978. doi: 10.1021/acsomega.4c02183. eCollection 2024 May 28.

DOI:10.1021/acsomega.4c02183
PMID:38826534
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11137725/
Abstract

The synthesis of new bicyclic lactone derivatives was carried out starting from 2-methyl/phenyl-3,4,7,7-tetrahydro-1-isoindole-1,3(2)-dione. 6-(Hydroxymethyl)--methyl/phenylcyclohex-3-ene-1-carboxamide derivatives were obtained from the reduction of tetrahydro-1-isoindole-1,3(2)-diones with NaBH. Bromination and epoxidation reactions of both compounds were examined, and the structures of the resulting products were determined by spectroscopic methods. Substituted bicyclic lactone compounds, which are interesting rearrangement products in both bromination and epoxidation reactions, were obtained. In particular, hydroxymethyl (-CHOH) and amide (-CONHR) groups attached to the cyclohexene ring in the bromination and epoxidation reactions were found to be effective in product formation. As a result, a new and applicable method was developed for the synthesis of bicyclic lactone derivatives.

摘要

新的双环内酯衍生物的合成是从2-甲基/苯基-3,4,7,7-四氢-1-异吲哚-1,3(2)-二酮开始进行的。6-(羟甲基)-2-甲基/苯基环己-3-烯-1-甲酰胺衍生物是通过用硼氢化钠还原四氢-1-异吲哚-1,3(2)-二酮得到的。研究了这两种化合物的溴化和环氧化反应，并通过光谱方法确定了所得产物的结构。获得了在溴化和环氧化反应中均为有趣重排产物的取代双环内酯化合物。特别地，发现在溴化和环氧化反应中连接到环己烯环上的羟甲基(-CHOH)和酰胺(-CONHR)基团在产物形成中是有效的。结果，开发了一种用于合成双环内酯衍生物的新的适用方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/09b1/11137725/b352151553c9/ao4c02183_0011.jpg
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