Tandem Hydrocyanation and Nitrile/Amide Cyclization of Propiolamides: A Rapid Access to 5‐Iminopyrrolones

Abstract A Pd‐catalyzed synthesis of 5‐iminopyrrolones from propiolamides was developed, which featured wide substrate scope and good yields. This efficient conversion involved a tandem hydrocyanation, E to Z isomerization of alkenes, and nitrile/amide cyclization. Control experiments show the intermediacy of β ‐cyanation products, and the Z‐isomers was efficiently converted to the target products by Pd/ L2 catalysis only after the cyanation reagent was completely consumed.

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Journal
ChemCatChem
Published
2024-08-26
DOI
https://doi.org/10.1002/cctc.202401255
Primary Topic
Synthesis and pharmacology of benzodiazepine derivatives
Type
article
Field-Weighted Citation Impact
0.00

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article

Tandem Hydrocyanation and Nitrile/Amide Cyclization of Propiolamides: A Rapid Access to 5‐Iminopyrrolones

Lingna Wang, Xianjie Fang, Jiawen Hu, Jinguo Long et al.
ChemCatChem
Synthesis and pharmacology of benzodiazepine derivatives
article

Tandem Hydrocyanation and Nitrile/Amide Cyclization of Propiolamides: A Rapid Access to 5‐Iminopyrrolones

Lingna Wang, Xianjie Fang, Jiawen Hu, Jinguo Long, Suliang Wang
article en

Abstract

Abstract A Pd‐catalyzed synthesis of 5‐iminopyrrolones from propiolamides was developed, which featured wide substrate scope and good yields. This efficient conversion involved a tandem hydrocyanation, E to Z isomerization of alkenes, and nitrile/amide cyclization. Control experiments show the intermediacy of β ‐cyanation products, and the Z‐isomers was efficiently converted to the target products by Pd/ L2 catalysis only after the cyanation reagent was completely consumed.

ChemCatChemVol. 16(23)
Hangzhou Normal University (CN), Hunan University (CN), State Key Laboratory of Chemobiosensing and Chemometrics (CN)
National Natural Science Foundation of China, China Postdoctoral Science Foundation, Natural Science Foundation of Hunan Province, Hangzhou Normal University
Openalex Percentile: Top 90%
Synthesis and pharmacology of benzodiazepine derivatives
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Tandem Hydrocyanation and Nitrile/Amide Cyclization of Propiolamides: A Rapid Access to 5‐Iminopyrrolones — Lingna Wang, Xianjie Fang, et al. · ChemCatChem (2024) | TGRS Research Map | TGRS