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[4 + 2] Annulation Reaction of In Situ Generated Azoalkenes with Azlactones: Access to 4,5-Dihydropyridazin-3(2H)‑Ones

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journal contribution
posted on 09.09.2020 by Wei-Cheng Yuan, Bao-Xue Quan, Jian-Qiang Zhao, Yong You, Zhen-Hua Wang, Ming-Qiang Zhou
An unprecedented [4 + 2] annulation reaction between in situ formed azoalkenes and azlactones has been developed. This reaction provides a facile access to an array of 4,5-dihydropyridazin-3­(2H)-one derivatives, which are very promising in medicinal applications as potential biologically active candidates. Notably, these dihydropyridazinones could also be synthesized via a one-pot reaction protocol by using the in situ formed azlactones from N-acyl amino acids and in situ generated azoalkenes from α-halogeno hydrazones. The potential applications of the methodology were also demonstrated by gram-scale experiments and the versatile conversions of the products into other nitrogen-containing compounds.