A new microwave-assisted, three-component reaction of 5-aminopyrazole-4-carboxylates : Selective synthesis of substituted 5-aza-9-deaza-adenines1

Lim, Felicia Phei Lin and Halcovitch, Nathan R. and Tiekink, Edward R.T. and Dolzhenko, Anton V. (2018) A new microwave-assisted, three-component reaction of 5-aminopyrazole-4-carboxylates : Selective synthesis of substituted 5-aza-9-deaza-adenines1. Tetrahedron, 74 (15). pp. 1868-1879. ISSN 0040-4020

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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.

Item Type:

Journal Article

Journal or Publication Title:

Tetrahedron

Additional Information:

This is the author’s version of a work that was accepted for publication in Tetrahedron. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron, 74, 15, 2018 DOI: 10.1016/j.tet.2018.02.054

Uncontrolled Keywords:

/dk/atira/pure/subjectarea/asjc/1300/1303

Subjects:

?? pyrazoletriazinepurine isosterepyrazolo[1,5-a][1,3,5]triazinemulticomponent reactiondynamic nmr spectroscopybiochemistryorganic chemistrydrug discovery ??

ID Code:

123821

Deposited By:

ep_importer_pure

Deposited On:

01 Mar 2018 13:52

Refereed?:

Yes

Published?:

Published

Last Modified:

19 Sep 2024 02:09

URI:

https://eprints.lancs.ac.uk/id/eprint/123821