A New, One-Pot, Multicomponent Synthesis of Bioactive N-Pyrazolylformamidines under Microwave Irradiation

Felicia Phei Lin Lim; Giuseppe Luna; Anton V. Dolzhenko

doi:10.1055/s-0035-1561616

Synthesis, Table of Contents

Synthesis 2016; 48(15): 2423-2428
DOI: 10.1055/s-0035-1561616

paper

A New, One-Pot, Multicomponent Synthesis of Bioactive N-Pyrazolylformamidines under Microwave Irradiation

Felicia Phei Lin Lim

^aSchool of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia Email: anton.dolzhenko@monash.edu Email: dolzhenkoav@gmail.com

,

Giuseppe Luna

^bSchool of Pharmacy, Curtin Health Innovation Research Institute, Faculty of Health Sciences, Curtin University, GPO Box U1987 Perth, Western Australia 6845, Australia

,

Anton V. Dolzhenko*

^aSchool of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia Email: anton.dolzhenko@monash.edu Email: dolzhenkoav@gmail.com

^bSchool of Pharmacy, Curtin Health Innovation Research Institute, Faculty of Health Sciences, Curtin University, GPO Box U1987 Perth, Western Australia 6845, Australia

^cFaculty of Pharmacy, South Ural State Medical University, 64 Vorovskogo Street, Chelyabinsk, 454092, Russian Federation

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Abstract

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Dedicated to Professor Viktor E. Kolla on the occasion of his 90^th birthday

Abstract

A one-pot, three-component, microwave-assisted reaction of polysubstituted 5-aminopyrazoles, triethyl orthoformate, and a series of cyclic secondary amines was developed and successfully employed for the synthesis of novel N-pyrazolylformamidines. Under catalyst-free conditions, the reaction proceeded in a chemo- and regioselective manner, resulting in the formation of unsymmetric formamidines, which were isolated in high yields and purity. Some of the prepared compounds were found to inhibit interleukin-17 secretion in phenotypic in vitro assays.

Key words

formamidines - pyrazoles - orthoesters - multicomponent reaction - microwave-assisted synthesis

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References

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