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

RSC Adv. 2019 Nov 19;9(64):37660-37667. doi: 10.1039/c9ra08795h. eCollection 2019 Nov 13.

Authors

Ahmad Junaid^{1

2}, Yee Seng Tan³, Edward R T Tiekink³, Anton V Dolzhenko^{1

4}

Affiliations

¹ School of Pharmacy, Monash University Malaysia Jalan Lagoon Selatan Bandar Sunway Selangor Darul Ehsan 47500 Malaysia anton.dolzhenko@monash.edu.
² Department of Chemistry, Prairie View A&M University P.O. Box 519 Prairie View Texas 77446 USA.
³ Research Centre for Crystalline Materials, School of Science and Technology, 5 Jalan Universiti, Sunway University Bandar Sunway Selangor Darul Ehsan 47500 Malaysia.
⁴ 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.

Abstract

A convenient one-pot method for the preparation of N ²,6-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.