Palladium-catalyzed amination of 2-chlorothienopyridone with primary aromatic amines

Abstract

A series of ethyl 7-cyclopropyl-2-(arylamino)-3-nitro-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate (9a-d) were prepared by coupling of ethyl 7-cyclopropyl-2-chloro-3-nitro-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate (8) with primary aromatic amines via palladium-catalyzed amination using palladium acetate Pd(OAc)₂ in the presence of cesium fluoride in good yields. The new compounds were characterized by ¹H-NMR, ¹³C-NMR, mass spectrometry, high resolution mass spectrometry and elemental analysis. 7-cyclopropyl-2-(phenylamino)-3-nitro-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid (10a) showed weak activity against E.aerogenas and S.aureus bacteria.

Keywords:

• 2-chloro-3-nitro-4-oxo-4
• 7-dihydrothieno[23-b]pyridines
• palladium catalyzed amination
• primary aromatic amines
• antibacterial activity

PUBLIC INTEREST STATEMENT

Antibiotic resistance is one of the biggest threats to global health, which is rising to alarming levels. The current research is the successful addition to the field of medicinal chemistry, in order to synthesize a new generation of antibiotics, which is bioisosters of fluoroquinolones antibiotics.

Competing interests

The authors declare no competing interests.

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Additional information

Funding

This work was supported by the Mutah Univercity/ Jordan [120/14/833].

Notes on contributors

Samir A. Al-Taweel

Samir A. Al-Taweel, the corresponding author, is working as Professor in Mutah University, Karak, Jordan. He has published more than 35 research papers in peer-reviewed international journals. He has guided ten MS students. The main focus of our research group is to develop simple and efficient synthetic strategies for the synthesis of new bioactive organic thiophene-based heterocyclic compounds. Recently, our research group interested in synthesizing dye-sensitizers, for the solar cell applications.

Salah A. Al-Trawneh

Salah A. Al-Trawneh is the co-author he is the associated professor in organic chemistry, the main interest of our research group is to develop simple and efficient synthetic protocol for the synthesis of new bioactive heterocyclic organic compounds.

Wal'A M. Al-Trawneh

Wal'A M. Al-Trawneh is a Master student conducting the synthesis and purification of the coupling products.