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Role of Pyridine Nitrogen in Palladium-Catalyzed Imine Hydrolysis: A Case Study of (E)-1-(3-bromothiophen-2-yl)-N-(4-methylpyridin-2-yl)methanimine

Ahmad G 1 , Rasool N 2 , Rizwan K 1 , Altaf AA 3 , Rashid U 4 , Mahmood T 5 Show all authors , Ayub K 5

Affiliations 

  • 1 Department of Chemistry, Government College University, Faisalabad 38000, Pakistan
  • 2 Department of Chemistry, Government College University, Faisalabad 38000, Pakistan. nasirrasool@gcuf.edu.pk
  • 3 Department of Chemistry, University of Gujrat, Hafiz Hayat Campus, Gujrat 50700, Pakistan
  • 4 Institute of Advanced Technology, University Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia. umer.rashid@upm.edu.my
  • 5 Department of Chemistry, COMSATS University Islamabad, Abbottabad Campus, University Road, Tobe Camp, Abbottabad 22060, Pakistan
Molecules, 2019 Jul 17;24(14).
PMID: 31319634 DOI: 10.3390/molecules24142609

Abstract

In the present study, 4-methylpyridin-2-amine was reacted with 3-bromothiophene-2-carbaldehyde and the Schiff base (E)-1-(3-bromothiophen-2-yl)-N-(4-methylpyridin-2-yl)methanimine was obtained in a 79% yield. Coupling of the Schiff base with aryl/het-aryl boronic acids under Suzuki coupling reaction conditions, using Pd(PPh3)4 as catalyst, yielded products with the hydrolysis of the imine linkages (5a-5k, 6a-6h) in good to moderate yields. To gain mechanistic insight into the transition metal-catalyzed hydrolysis of the compounds, density functional theory (DFT) calculations were performed. The theoretical calculations strongly supported the experiment and provided an insight into the transition metal-catalyzed hydrolysis of imines.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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