I2-Promoted [4 + 2] cycloaddition of in situ generated azoalkenes with enaminones: facile and efficient synthesis of 1,4-dihydropyridazines and pyridazines

Jiajun Feng; Tiantong He; Yuxing Xie; Yang Yu; Jonathan B. Baell; Fei Huang

doi:10.1039/D0OB01958E

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I₂-Promoted [4 + 2] cycloaddition of in situ generated azoalkenes with enaminones: facile and efficient synthesis of 1,4-dihydropyridazines and pyridazines†

Jiajun Feng,^a Tiantong He,^a Yuxing Xie,^b Yang Yu,

^c Jonathan B. Baell

^ad and Fei Huang

*^ab

Author affiliations

* Corresponding authors

^a School of Pharmaceutical Sciences, Nanjing Tech University, Nanjing 211816, P. R. China
E-mail: huangfei0208@yeah.net

^b School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, Nanjing 210023, P. R. China

^c School of Environmental Science and Engineering, Nanjing Tech University, Nanjing 211816, P. R. China

^d Medicinal Chemistry Theme, Monash Institute of Pharmaceutical Sciences, Monash University, Parkville, Victoria 3052, Australia

Abstract

A facile and efficient strategy for the synthesis of 1,4-dihydropyridazines and pyridazines through I₂-promoted [4 + 2] cycloaddition of in situ generated azoalkenes with enaminones has been developed. The switch in selectivity is attributed to the judicious choice of different reaction temperatures. The key features of this work include controllable and selective synthesis, good functional group tolerance, good to excellent reaction yields, metal/base-free conditions, and also applicability to one-pot methodology.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/D0OB01958E
Article type: Paper
Submitted: 23 Sep 2020
Accepted: 28 Oct 2020
First published: 29 Oct 2020

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Org. Biomol. Chem., 2020,18, 9483-9493

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I₂-Promoted [4 + 2] cycloaddition of in situ generated azoalkenes with enaminones: facile and efficient synthesis of 1,4-dihydropyridazines and pyridazines

J. Feng, T. He, Y. Xie, Y. Yu, J. B. Baell and F. Huang, Org. Biomol. Chem., 2020, 18, 9483 DOI: 10.1039/D0OB01958E

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Organic & Biomolecular Chemistry