Issue 10, 2024

Concise synthesis of pyrrolo[3,4-c]quinolines via a P(NMe2)3-catalyzed [4 + 2] annulation followed by a Zn/AcOH-mediated reduction–hydroamination–isomerization

Abstract

A P(NMe2)3-catalyzed [4 + 2] annulation of 2-amino-β-nitrostyrenes and β′-acetoxy allenoates followed by a Zn/AcOH-mediated reduction–hydroamination–isomerization has been developed. A range of tetrahydroquinolines and pyrrolo[3,4-c]quinolines bearing an all-carbon quaternary stereogenic center were smoothly synthesized in moderate yields. The protocol is a practical and scalable strategy, and establishes a core structural moiety of natural products and bioactive molecules.

Graphical abstract: Concise synthesis of pyrrolo[3,4-c]quinolines via a P(NMe2)3-catalyzed [4 + 2] annulation followed by a Zn/AcOH-mediated reduction–hydroamination–isomerization

Supplementary files

Article information

Article type
Research Article
Submitted
26 Jan 2024
Accepted
15 Mar 2024
First published
18 Mar 2024

Org. Chem. Front., 2024,11, 2762-2767

Concise synthesis of pyrrolo[3,4-c]quinolines via a P(NMe2)3-catalyzed [4 + 2] annulation followed by a Zn/AcOH-mediated reduction–hydroamination–isomerization

Z. Chen, D. Xiong, N. Wang, Y. Zhang, H. Yao, J. Zhang, N. Huang and K. Zou, Org. Chem. Front., 2024, 11, 2762 DOI: 10.1039/D4QO00169A

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