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Journal of the Iranian Chemical Society

, Volume 15, Issue 7, pp 1647–1654 | Cite as

A facile and expedient microwave-assisted solvent-free method for the synthesis of 2-amino-4-(2-oxo-2H-chromen-3-yl)nicotinonitriles

  • Devulapally Srikrishna
  • Pramod Kumar Dubey
Original Paper
  • 63 Downloads

Abstract

An efficient method for the synthesis of novel 2-amino-4-(2-oxo-2H-chromen-3-yl)nicotinonitriles has been developed under solvent-free conditions using enaminonitriles and various aliphatic amines. 3-acetyl-2H-chromen-2-one (1) reacted with malononitirle in ethanol using l-proline as a base to give 2-(1-(2-oxo-2H-chromen-3-yl)ethylidene)malononitrile (2) which on reaction with dimethylformamide dimethyl acetal (DMF-DMA) resulted in the formation of 2-(3-(dimethylamino)-1-(2-oxo-2H-chromen-3-yl)allylidene)malononitrile (3). The later on reaction with various aliphatic amines under solvent-free conditions gave the title compounds, i.e., 2-amino-4-(2-oxo-2H-chromen-3-yl)nicotinonitriles (4). Microwave irradiation method has also been applied successfully to achieve the compounds in excellent yields.

Graphical Abstract

Keywords

Coumarins 2-Amino-3-cyanopyridines Solvent-free method Microwave irradiation 

Notes

Acknowledgements

The authors are thankful to the authorities of Jawaharlal Nehru Technological University Hyderabad for providing laboratory facilities. They are grateful to the Department of Science & Technology, Govt. of India, New Delhi, for the financial support in the form of INSPIRE Fellowship to one of them (D.S.).

Supplementary material

13738_2018_1363_MOESM1_ESM.doc (46.2 mb)
Supplementary material 1 (DOC 47268 kb)

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Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  1. 1.Department of ChemistryJawaharlal Nehru Technological University Hyderabad College of EngineeringKukatpally, HyderabadIndia

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