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基于二苯并环庚烯酮的新型多环π共轭二氢哒嗪、哒嗪和吡咯的合成。

Synthesis of dibenzosuberenone-based novel polycyclic π-conjugated dihydropyridazines, pyridazines and pyrroles.

作者信息

Koçak Ramazan, Daştan Arif

机构信息

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

出版信息

Beilstein J Org Chem. 2021 Mar 15;17:719-729. doi: 10.3762/bjoc.17.61. eCollection 2021.

DOI:10.3762/bjoc.17.61
PMID:33796159
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7991620/
Abstract

The synthesis of novel polycyclic π-conjugated dihydropyridazines, pyridazines, and pyrroles was studied. Dihydropyridazine dyes were synthesized by inverse electron-demand Diels-Alder cycloaddition reactions between a dibenzosuberenone and tetrazines that bear various substituents. The pyridazines were synthesized in high yields by oxidation of dihydropyridazine-appended dibenzosuberenones with PIFA or NO. -Quinone derivatives of pyridazines were also obtained by H-shift isomerization following the inverse electron-demand Diels-Alder reaction of tetrazines with -quinone dibenzosuberenone. Then these pyridazines were converted to the corresponding pyrroles by reductive treatment with zinc. It was observed that all the dihydropyridazines obtained gave absorbance and emission at long wavelengths.

摘要

对新型多环π共轭二氢哒嗪、哒嗪和吡咯的合成进行了研究。二氢哒嗪染料是通过二苯并亚甲基酮与带有各种取代基的四嗪之间的逆电子需求狄尔斯-阿尔德环加成反应合成的。通过用PIFA或NO氧化带有二氢哒嗪的二苯并亚甲基酮，高产率地合成了哒嗪。哒嗪的醌衍生物也是通过四嗪与醌二苯并亚甲基酮的逆电子需求狄尔斯-阿尔德反应后的H-迁移异构化得到的。然后，通过用锌进行还原处理，将这些哒嗪转化为相应的吡咯。观察到所得到的所有二氢哒嗪在长波长处都有吸收和发射。

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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60a7/7991620/aa5746691201/Beilstein_J_Org_Chem-17-719-g006.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60a7/7991620/928b323a2cc9/Beilstein_J_Org_Chem-17-719-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60a7/7991620/d71523d32064/Beilstein_J_Org_Chem-17-719-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60a7/7991620/82d23e3f76fc/Beilstein_J_Org_Chem-17-719-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60a7/7991620/9ef1472f49a3/Beilstein_J_Org_Chem-17-719-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60a7/7991620/d432d6214af1/Beilstein_J_Org_Chem-17-719-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60a7/7991620/f43b1596de47/Beilstein_J_Org_Chem-17-719-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60a7/7991620/505dcfe5aae7/Beilstein_J_Org_Chem-17-719-g012.jpg
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