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通过卡斯塔尼奥利-库什曼反应一步合成三环稠合的1,2,3,4-四氢异喹啉体系。

One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli-Cushman protocol.

作者信息

Pashev Aleksandar, Burdzhiev Nikola, Stanoeva Elena

机构信息

Sofia University "St. Kliment Ohridski", Faculty of Chemistry and Pharmacy, 1, James Bourchier ave., 1164 Sofia, Bulgaria.

Medical University Pleven, Faculty of Pharmacy, 1, St. Kliment Ohridski str., 5800 Pleven, Bulgaria.

出版信息

Beilstein J Org Chem. 2020 Jun 24;16:1456-1464. doi: 10.3762/bjoc.16.121. eCollection 2020.

DOI:10.3762/bjoc.16.121
PMID:32647547
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7323625/
Abstract

The Castagnoli-Cushman reaction of 3,4-dihydroisoquinolines with glutaric anhydride, its oxygen and sulfur analogues was investigated as a one-step approach to the benzo[]quinolizidine system and its heterocyclic analogs. An extension towards the pyrrolo[2,1-]isoquinoline system was achieved with the use of succinic anhydride. The results are evidence of an unexplored method for the access of the aforementioned tricyclic annelated systems incorporating a bridgehead nitrogen atom. The structures and relative configurations of the new compounds were established by means of 1D and 2D NMR techniques. The reactions between 1-methyldihydroisoquinoline and glutaric, diglycolic and succinic anhydrides yielded unexpected isoquinoline derivatives containing an exocyclic double bond. The compounds prepared bear the potential to become building blocks for future synthetic bioactive molecules.

摘要

研究了3,4-二氢异喹啉与戊二酸酐及其氧和硫类似物的Castagnoli-Cushman反应，作为一种一步合成苯并[]喹嗪系统及其杂环类似物的方法。通过使用琥珀酸酐实现了向吡咯并[2,1-]异喹啉系统的扩展。这些结果证明了一种未被探索的方法，可用于合成包含桥头氮原子的上述三环稠合系统。通过一维和二维核磁共振技术确定了新化合物的结构和相对构型。1-甲基二氢异喹啉与戊二酸酐、二甘醇酸酐和琥珀酸酐之间的反应产生了含有环外双键的意外异喹啉衍生物。所制备的化合物有可能成为未来合成生物活性分子的构建模块。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/6aaca632f5b9/Beilstein_J_Org_Chem-16-1456-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/a39726ab63ab/Beilstein_J_Org_Chem-16-1456-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/03c93788c8e7/Beilstein_J_Org_Chem-16-1456-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/f960a45426f7/Beilstein_J_Org_Chem-16-1456-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/16633a6cd479/Beilstein_J_Org_Chem-16-1456-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/243406481fd3/Beilstein_J_Org_Chem-16-1456-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/64deda928723/Beilstein_J_Org_Chem-16-1456-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/f0303e1f3463/Beilstein_J_Org_Chem-16-1456-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/cb110d336c7e/Beilstein_J_Org_Chem-16-1456-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/a0d9a1e90f40/Beilstein_J_Org_Chem-16-1456-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/009408297d3d/Beilstein_J_Org_Chem-16-1456-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/6aaca632f5b9/Beilstein_J_Org_Chem-16-1456-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/a39726ab63ab/Beilstein_J_Org_Chem-16-1456-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/03c93788c8e7/Beilstein_J_Org_Chem-16-1456-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/f960a45426f7/Beilstein_J_Org_Chem-16-1456-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/16633a6cd479/Beilstein_J_Org_Chem-16-1456-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/243406481fd3/Beilstein_J_Org_Chem-16-1456-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/64deda928723/Beilstein_J_Org_Chem-16-1456-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/f0303e1f3463/Beilstein_J_Org_Chem-16-1456-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/cb110d336c7e/Beilstein_J_Org_Chem-16-1456-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/a0d9a1e90f40/Beilstein_J_Org_Chem-16-1456-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/009408297d3d/Beilstein_J_Org_Chem-16-1456-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acb0/7323625/6aaca632f5b9/Beilstein_J_Org_Chem-16-1456-g012.jpg

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