Phosphine-catalyzed [4 + 3] and [4 + 4] annulations of β′-acetoxy allenoates with N,N-dinucleophiles: access to 1,3-diazepine and 1,4-diazocine derivatives

Chunjie Ni; Zhanhang Liang; Xiaojuan Xu; Fan Yu; Yining Zhao; Chen Chen

doi:10.1039/D4QO00949E

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Phosphine-catalyzed [4 + 3] and [4 + 4] annulations of β′-acetoxy allenoates with N,N-dinucleophiles: access to 1,3-diazepine and 1,4-diazocine derivatives†

Chunjie Ni,

*^a Zhanhang Liang,^a Xiaojuan Xu,^a Fan Yu,^a Yining Zhao*^a and Chen Chen*^b

Author affiliations

* Corresponding authors

^a School of Pharmacy, Yancheng Teachers University, Yancheng 224007, P. R. China
E-mail: chunjie_ni@hotmail.com, nicj@yctu.edu.cn

^b Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, P. R. China
E-mail: hxxycc@tjnu.edu.cn

Abstract

Novel methods for constructing functionalized 1,3-diazepine and 1,4-diazocine derivatives have been disclosed through phosphine-catalyzed [4 + 3] and [4 + 4] annulations of β′-acetoxy allenoates with N,N-dinucleophiles. These approaches demonstrate high efficiency and yields ranging from good to excellent. The biological evaluation indicates that three of the developed cycloadducts exhibit satisfactory inhibitory activities against three human cancer cell lines (HCT116, A549 and HepG2) beyond those of 5-fluorouracil.

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DOI: https://doi.org/10.1039/D4QO00949E
Article type: Research Article
Submitted: 26 May 2024
Accepted: 22 Jul 2024
First published: 24 Jul 2024

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Org. Chem. Front., 2024, Advance Article

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Phosphine-catalyzed [4 + 3] and [4 + 4] annulations of β′-acetoxy allenoates with N,N-dinucleophiles: access to 1,3-diazepine and 1,4-diazocine derivatives

C. Ni, Z. Liang, X. Xu, F. Yu, Y. Zhao and C. Chen, Org. Chem. Front., 2024, Advance Article , DOI: 10.1039/D4QO00949E

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Phosphine-catalyzed [4 + 3] and [4 + 4] annulations of β′-acetoxy allenoates with N,N-dinucleophiles: access to 1,3-diazepine and 1,4-diazocine derivatives†

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Phosphine-catalyzed [4 + 3] and [4 + 4] annulations of β′-acetoxy allenoates with N,N-dinucleophiles: access to 1,3-diazepine and 1,4-diazocine derivatives

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