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通过 Vilsmeier 反应实现哒嗪-1,4-二酮和邻氨基苯甲酰亚胺的结构鉴定：氮环化和互变异构研究。

Structural Identification between Phthalazine-1,4-Diones and -Aminophthalimides via Vilsmeier Reaction: Nitrogen Cyclization and Tautomerization Study.

机构信息

School of Pharmacy, China Medical University, No. 91, Hsueh-Shih Rd., Taichung 40402, Taiwan.

The Ph.D. Program for Biotech Pharmaceutical Industry and School of Pharmacy, China Medical University, No. 91, Hsueh-Shih Rd., Taichung 40402, Taiwan.

出版信息

Molecules. 2021 May 13;26(10):2907. doi: 10.3390/molecules26102907.

DOI:10.3390/molecules26102907
PMID:34068439
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8153572/
Abstract

-Aminophthalimides and phthalazine 1,4-diones were synthesized from isobenzofuran-1,3-dione, isoindoline-1,3-dione, furo [3,4-] pyrazine-5,7-dione, or 1-pyrrolo [3,4-] pyridine-1,3-dione with monohydrate hydrazine to carry out the 5-exo or 6-endo nitrogen cyclization under the different reaction conditions. Based on the control experimental results, 6-endo thermodynamic hydrohydrazination and kinetical 5-exo cyclization reactions were individually selective formation. Subsequently, Vilsmeier amidination derivatization was successfully developed to probe the structural divergence between -aminophthalimide and phthalazine 1,4-dione . On the other hand, the best tautomerization of -aminophthalimide to diazinone was also determined under acetic acid mediated solution.

摘要
  • 从异苯并呋喃-1,3-二酮、异吲哚啉-1,3-二酮、呋喃[3,4-]吡嗪-5,7-二酮或 1-吡咯[3,4-]吡啶-1,3-二酮与一水合肼合成氨基邻苯二甲酰亚胺和邻苯二甲酰亚胺 1,4-二酮，在不同的反应条件下进行 5-外或 6-内氮环化。根据对照实验结果，分别选择性地形成了 6-内热力学氢肼化和动力学 5-外环化反应。随后，成功开发了 Vilsmeier 酰胺化衍生化方法，以探究 -氨基邻苯二甲酰亚胺和邻苯二甲酰亚胺 1,4-二酮之间的结构差异。另一方面，还确定了在乙酸介导的溶液中 -氨基邻苯二甲酰亚胺到哒嗪酮的最佳互变异构化。
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c28f/8153572/20ef3fe9cfe9/molecules-26-02907-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c28f/8153572/5db287063616/molecules-26-02907-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c28f/8153572/0fa45180cac5/molecules-26-02907-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c28f/8153572/14da5c897c02/molecules-26-02907-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c28f/8153572/0aee40684730/molecules-26-02907-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c28f/8153572/20ef3fe9cfe9/molecules-26-02907-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c28f/8153572/5db287063616/molecules-26-02907-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c28f/8153572/0fa45180cac5/molecules-26-02907-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c28f/8153572/14da5c897c02/molecules-26-02907-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c28f/8153572/0aee40684730/molecules-26-02907-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c28f/8153572/20ef3fe9cfe9/molecules-26-02907-g004.jpg

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