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A new microwave-assisted,three-component reaction of 5-aminopyrazole-4-carboxylates: Selective synthesis of substituted 5-aza-9-deaza-adenines
Authors:Felicia Phei Lin Lim  Nathan R Halcovitch  Edward RT Tiekink  Anton V Dolzhenko
Institution:1. School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor Darul Ehsan, 47500, Malaysia;2. Department of Chemistry, Lancaster University, Lancaster, LA1 4YB, United Kingdom;3. Research Centre for Crystalline Materials, School of Science and Technology, Sunway University, Bandar Sunway, Selangor Darul Ehsan, 47500, Malaysia;4. School of Pharmacy, Curtin Health Innovation Research Institute, Faculty of Health Sciences, Curtin University, GPO Box U1987, Perth, Western Australia, 6845, Australia
Abstract:A series of 5-aza-9-deaza- analogues of purine was effectively prepared using highly selective annulation of 1,3,5-triazine ring onto 5-aminopyrazole-4-carboxylates via a one-pot, multicomponent, microwave-assisted approach. The products were obtained in good yields and high purity. This catalyst-free method was demonstrated to be scalable and highly reproducible in different microwave reactors. Some structural features of the prepared compounds were studied in details using dynamic NMR spectroscopy and X-ray crystallography.
Keywords:Pyrazole  Triazine  Purine isostere  Multicomponent reaction  Dynamic NMR spectroscopy  BQWNLWWMIFNTFW-UHFFFAOYSA-N  YEPBDQFOORDIHJ-UHFFFAOYSA-N  FTNBJEVFRJEVOF-UHFFFAOYSA-N  BGQATFJGRTYWQK-UHFFFAOYSA-N  PTDYKJXYOIFPSS-UHFFFAOYSA-N  WJOSYOWGFHJPEP-UHFFFAOYSA-N  XWHPLSKZHNINGL-UHFFFAOYSA-N  QEBSNPLXEZQRMW-UHFFFAOYSA-N  WRORVOFZNGGMGB-UHFFFAOYSA-N  LGHGDXPQPORZJK-UHFFFAOYSA-N  FWOBUKLXHOHMLQ-UHFFFAOYSA-N  LXAILASNSHFQQT-UHFFFAOYSA-N  KIROZRBIGCKNCD-UHFFFAOYSA-N  TXKHAIOSNPUPKB-UHFFFAOYSA-N  QXSYNJLZDUWIJB-UHFFFAOYSA-N  ZBTPXHLVGHPDAX-UHFFFAOYSA-N  QFAOUQMRAFSVAM-UHFFFAOYSA-N  RONBGSCUQJHENE-UHFFFAOYSA-N  UYAKKEYDLXBOME-UHFFFAOYSA-N  AYXBJEYKERFXSI-UHFFFAOYSA-N  DXMQVDBZEGRVAS-UHFFFAOYSA-N  CEGRRSMNQLGZFT-UHFFFAOYSA-N  IBVOCNMDIUFZQU-UHFFFAOYSA-N  VFJSMZSWBAIKEU-UHFFFAOYSA-N
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