A one-pot synthesis of N2,6-diaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines and systematic evaluation of their ability to host ethanol in crystals

Ahmad Junaid; Yee Seng Tan; Edward R. T. Tiekink; Anton V. Dolzhenko

doi:10.1039/C9RA08795H

A one-pot synthesis of N²,6-diaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines and systematic evaluation of their ability to host ethanol in crystals†

Ahmad Junaid,^ad Yee Seng Tan,^b Edward R. T. Tiekink

^b and Anton V. Dolzhenko

*^ac

Author affiliations

* Corresponding authors

^a School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia
E-mail: anton.dolzhenko@monash.edu

^b Research Centre for Crystalline Materials, School of Science and Technology, 5 Jalan Universiti, Sunway University, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia

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

^d Department of Chemistry, Prairie View A&M University, P.O. Box 519, Prairie View, Texas 77446, USA

Abstract

A convenient one-pot method for the preparation of N²,6-diaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines was developed using a three-component synthesis of 1,6-diaryl-1,6-dihydro-1,3,5-triazine-2,4-diamines followed by their Dimroth rearrangement to the desired products. The prepared compounds crystallized from ethanol as ethanol clathrates (1 : 1). X-ray crystallography on several products confirmed the adoption of 5,6-dihydro-tautomer. The thermal analysis and powder X-ray diffraction experiments on selected compounds suggested that thermal desolvation of crystals was irreversible.

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DOI: https://doi.org/10.1039/C9RA08795H
Article type: Paper
Submitted: 26 Oct 2019
Accepted: 13 Nov 2019
First published: 19 Nov 2019
This article is Open Access

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RSC Adv., 2019,9, 37660-37667

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A one-pot synthesis of N²,6-diaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines and systematic evaluation of their ability to host ethanol in crystals

A. Junaid, Y. S. Tan, E. R. T. Tiekink and A. V. Dolzhenko, RSC Adv., 2019, 9, 37660 DOI: 10.1039/C9RA08795H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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A one-pot synthesis of N²,6-diaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines and systematic evaluation of their ability to host ethanol in crystals†

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A one-pot synthesis of N²,6-diaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines and systematic evaluation of their ability to host ethanol in crystals

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