Photo-induced phosphorylation/cyclization of N-homoallyl and N-allyl aldehyde hydrazones to access phosphorylated tetrahydropyridazines and dihydropyrazoles

Lingli Liu; Yechun Wu; Chengli Xiang; Jin-Tao Yu; Changduo Pan

doi:10.1039/D4CC00608A

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Photo-induced phosphorylation/cyclization of N-homoallyl and N-allyl aldehyde hydrazones to access phosphorylated tetrahydropyridazines and dihydropyrazoles†

Lingli Liu,^a Yechun Wu,^a Chengli Xiang,^a Jin-Tao Yu

*^a and Changduo Pan

*^b

Author affiliations

* Corresponding authors

^a School of Petrochemical Engineering, Changzhou University, Changzhou 213164, P. R. China
E-mail: yujintao@cczu.edu.cn

^b School of Chemistry and Chemical Engineering, Jiangsu University of Technology, Changzhou 213001, P. R. China
E-mail: panchangduo@jsut.edu.cn

Abstract

A photocatalytic radical carbophosphorylation/cyclization of N-homoallyl aldehyde hydrazones with phosphine oxides was developed under metal-free conditions, achieving phosphorylated tetrahydropyridazines in yields up to 95%. Phosphorylated dihydropyrazoles were also constructed, by reacting N-allyl aldehyde hydrazones with phosphine oxides under the same conditions.

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Supplementary files

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Article information

DOI: https://doi.org/10.1039/D4CC00608A
Article type: Communication
Submitted: 06 Feb 2024
Accepted: 02 Apr 2024
First published: 03 Apr 2024

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Chem. Commun., 2024,60, 4687-4690

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Photo-induced phosphorylation/cyclization of N-homoallyl and N-allyl aldehyde hydrazones to access phosphorylated tetrahydropyridazines and dihydropyrazoles

L. Liu, Y. Wu, C. Xiang, J. Yu and C. Pan, Chem. Commun., 2024, 60, 4687 DOI: 10.1039/D4CC00608A

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Chemical Communications

Photo-induced phosphorylation/cyclization of N-homoallyl and N-allyl aldehyde hydrazones to access phosphorylated tetrahydropyridazines and dihydropyrazoles†

Abstract

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Photo-induced phosphorylation/cyclization of N-homoallyl and N-allyl aldehyde hydrazones to access phosphorylated tetrahydropyridazines and dihydropyrazoles

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