A New One-Pot Three-Component Synthesis of 4-Aryl-6-cycloamino-1,3,5-triazin-2-amines under Microwave Irradiation

Muhammad Syafiq Bin Shahari; Ahmad Junaid; Edward R. T. Tiekink; Anton V. Dolzhenko

doi:10.1055/a-1401-2795

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(14): 2457-2468
DOI: 10.1055/a-1401-2795

paper

A New One-Pot Three-Component Synthesis of 4-Aryl-6-cycloamino-1,3,5-triazin-2-amines under Microwave Irradiation

Muhammad Syafiq Bin Shahari

^aSchool of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia

,

Ahmad Junaid

^bDepartment of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, Indiana 47907, USA

,

Edward R. T. Tiekink

^cResearch Centre for Crystalline Materials, School of Medical and Life Sciences, Sunway University, 5 Jalan Universiti, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia

,

Anton V. Dolzhenko ∗

^aSchool of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia

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

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Abstract

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Dedicated to the memory of Professor Boris Syropyatov (6 Nov 1940 – 24 Oct 2020)

Abstract

A new method for the fast synthesis of diverse 4-aryl-6-cycloamino-1,3,5-triazin-2-amines was developed. The synthesis is performed under microwave irradiation in a one-pot manner from cyanoguanidine, aromatic aldehydes, and cyclic amines. Their three-component reaction in the presence of hydrochloric acid produced dihydrotriazines, which were then converted (without isolation) into the targeted compounds via aromatic dehydrogenation in the presence of alkali. The reaction tolerated various aromatic aldehydes (including heterocyclic) and cyclic amines. Crystal structures of two representative 4-aryl-6-morpholino-1,3,5-triazin-2-amines were established by X-ray crystallography. The results of preliminary biological screening identified potent antileukemic activity for 6-[3,4-dihydroisoquinolin-2(1H)-yl]-4-phenyl-1,3,5-triazin-2-amine.

Key words

triazines - multicomponent reactions - microwave-assisted synthesis - dehydrogenative aromatization - antiproliferative activity

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