A new microwave-assisted, three-component reaction of 5-aminopyrazole-4-carboxylates: Selective synthesis of substituted 5-aza-9-deaza-adenines

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-fr...

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Bibliographic Details
Published in:Tetrahedron 2018-04, Vol.74 (15), p.1868-1879
Main Authors: Lim, Felicia Phei Lin, Halcovitch, Nathan R., Tiekink, Edward R.T., Dolzhenko, Anton V.
Format: Article
Language:English
Subjects:
Dynamic NMR spectroscopy
Multicomponent reaction
Purine isostere
Pyrazole
Pyrazolo[1,5-a][1,3,5]triazine
Triazine
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Summary: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. [Display omitted] •A practical synthesis of adenine analogues.•A new scalable and reproducible microwave-assisted synthesis.•A hindered rotation study by dynamic NMR spectroscopy.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.02.054