Photoinduced Decarbonylative Rearrangement of Diazabicyclo[2.2.2]Octenones: A Photochemical Approach of Diazabicyclo[4.1.0]heptene Skeleton from Masked o‑Benzoquinone

We report a photoinduced decarbonylative rearrangement of diazabicyclo[2.2.2]­octenone in the facile synthesis of a functionalized diazabicyclo[4.1.0]­heptene skeleton, a unique derivative of the hydropyridazine type structure which could be found in a variety of biologically active natural products...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-01, Vol.88 (2), p.1235-1244
Main Authors: Wun, Bo-Jyun, Hu, Yung-Chen, Chi, Chu-Yun, Chuang, Gary Jing
Format: Article
Language:English
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Summary:We report a photoinduced decarbonylative rearrangement of diazabicyclo[2.2.2]­octenone in the facile synthesis of a functionalized diazabicyclo[4.1.0]­heptene skeleton, a unique derivative of the hydropyridazine type structure which could be found in a variety of biologically active natural products. The scope of functional group compatibility in the photoreaction was examined by taking advantage of the easy access of the heterobicyclo[2.2.2] structure from the Diels–Alder reaction of masked o-benzoquinones. 4-Phenyl-1,2,4-triazoline-3,5-dione served as the dienophile which provided the adjacent N–N unit in hexahydropyridazine-type products of subsequent photorearrangement.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02373