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吡咯并苯并噻嗪与席夫碱和碳二亚胺的反应：构建角型6/5/5/5-四环螺杂环的方法。

Reaction of Pyrrolobenzothiazines with Schiff Bases and Carbodiimides: Approach to Angular 6/5/5/5-Tetracyclic Spiroheterocycles.

作者信息

Lystsova Ekaterina A, Novokshonova Anastasia D, Khramtsov Pavel V, Novikov Alexander S, Dmitriev Maksim V, Maslivets Andrey N, Khramtsova Ekaterina E

机构信息

Department of Chemistry, Perm State University, ul. Bukireva, 15, 614990 Perm, Russia.

Department of Biology, Perm State University, ul. Bukireva, 15, 614990 Perm, Russia.

出版信息

Molecules. 2024 May 1;29(9):2089. doi: 10.3390/molecules29092089.

DOI:10.3390/molecules29092089
PMID:38731580
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11085407/
Abstract

1-Pyrrole-2,3-diones, fused at []-side with a heterocycle, are suitable platforms for the synthesis of various angular polycyclic alkaloid-like spiroheterocycles. Recently discovered sulfur-containing []-fused 1-pyrrole-2,3-diones (aroylpyrrolobenzothiazinetriones) tend to exhibit unusual reactivity. Based on these peculiar representatives of []-fused 1-pyrrole-2,3-diones, we have developed an approach to an unprecedented 6/5/5/5-tetracyclic alkaloid-like spiroheterocyclic system of benzo[]pyrrolo[3',4':2,3]pyrrolo[2,1-]thiazole via their reaction with Schiff bases and carbodiimides. The experimental results have been supplemented with DFT computational studies. The synthesized alkaloid-like 6/5/5/5-tetracyclic compounds have been tested for their biotechnological potential as growth stimulants in the green algae .

摘要

与杂环在[]侧稠合的1-吡咯-2,3-二酮是合成各种角型多环生物碱样螺杂环的合适平台。最近发现的含硫[]稠合的1-吡咯-2,3-二酮（芳酰基吡咯并苯并噻嗪三酮）往往表现出异常的反应性。基于这些[]稠合的1-吡咯-2,3-二酮的特殊代表，我们通过它们与席夫碱和碳二亚胺的反应，开发了一种合成前所未有的苯并[]吡咯并[3',4':2,3]吡咯并[2,1-]噻唑6/5/5/5-四环生物碱样螺杂环体系的方法。实验结果得到了DFT计算研究的补充。已对合成的生物碱样6/5/5/5-四环化合物作为绿藻生长刺激剂的生物技术潜力进行了测试。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/98b3db4986a9/molecules-29-02089-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/5c3c6adb2e83/molecules-29-02089-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/819cb21bb60c/molecules-29-02089-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/991fb3394e4a/molecules-29-02089-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/fd65cce1cdcc/molecules-29-02089-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/5c491a09307e/molecules-29-02089-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/133b75d54dee/molecules-29-02089-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/cd14adf3f7bf/molecules-29-02089-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/52e94debac59/molecules-29-02089-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/5da6439e4ef4/molecules-29-02089-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/44b531a52b11/molecules-29-02089-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/240037c3b3f0/molecules-29-02089-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/a4d31ae499ca/molecules-29-02089-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/98b3db4986a9/molecules-29-02089-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/5c3c6adb2e83/molecules-29-02089-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/819cb21bb60c/molecules-29-02089-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/991fb3394e4a/molecules-29-02089-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/fd65cce1cdcc/molecules-29-02089-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/5c491a09307e/molecules-29-02089-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/133b75d54dee/molecules-29-02089-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/cd14adf3f7bf/molecules-29-02089-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/52e94debac59/molecules-29-02089-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/5da6439e4ef4/molecules-29-02089-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/44b531a52b11/molecules-29-02089-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/240037c3b3f0/molecules-29-02089-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/a4d31ae499ca/molecules-29-02089-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9afe/11085407/98b3db4986a9/molecules-29-02089-sch008.jpg

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