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

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, Anton V. Dolzhenko, Yee Seng Tan, Edward R.T. Tiekink

Malaysia Sch of Pharmacy

Research output: Contribution to journal › Article › Research › peer-review

6 Citations (Scopus)

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.

Original language	English
Pages (from-to)	37660-37667
Number of pages	8
Journal	RSC Advances
Volume	9
Issue number	64
DOIs	https://doi.org/10.1039/c9ra08795h
Publication status	Published - 18 Nov 2019

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10.1039/c9ra08795hLicence: CC BY

345065070-oaFinal published version, 426 KBLicence: CC BY

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title = "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",

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.",

author = "Ahmad Junaid and Dolzhenko, {Anton V.} and Tan, {Yee Seng} and Tiekink, {Edward R.T.}",

note = "Funding Information: This work is supported by the Ministry of Higher Education, Malaysia under Fundamental Research Grant Scheme, grant number FRGS/1/2015/SG01/MUSM/03/1. The authors thank Sunway University Sdn Bhd (grant number STR-RCTR-RCCM-001-2019) for support of crystallographic studies. Publisher Copyright: This journal is {\textcopyright} The Royal Society of Chemistry. Copyright: Copyright 2019 Elsevier B.V., All rights reserved.",

year = "2019",

month = nov,

day = "18",

doi = "10.1039/c9ra08795h",

language = "English",

volume = "9",

pages = "37660--37667",

journal = "RSC Advances",

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T1 - 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

AU - Junaid, Ahmad

AU - Dolzhenko, Anton V.

AU - Tan, Yee Seng

AU - Tiekink, Edward R.T.

N1 - Funding Information: This work is supported by the Ministry of Higher Education, Malaysia under Fundamental Research Grant Scheme, grant number FRGS/1/2015/SG01/MUSM/03/1. The authors thank Sunway University Sdn Bhd (grant number STR-RCTR-RCCM-001-2019) for support of crystallographic studies. Publisher Copyright: This journal is © The Royal Society of Chemistry. Copyright: Copyright 2019 Elsevier B.V., All rights reserved.

PY - 2019/11/18

Y1 - 2019/11/18

N2 - 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.

AB - 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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DO - 10.1039/c9ra08795h

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SN - 2046-2069

VL - 9

SP - 37660

EP - 37667

JO - RSC Advances

JF - RSC Advances

IS - 64

ER -

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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Synthesis of 5-azapurine derivatives as new modulators of purinergic receptors

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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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Synthesis of 5-azapurine derivatives as new modulators of purinergic receptors

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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