Rights statement: 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
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Final published version
Research output: Contribution to Journal/Magazine › Journal article › peer-review
Research output: Contribution to Journal/Magazine › Journal article › peer-review
}
TY - JOUR
T1 - A new microwave-assisted, three-component reaction of 5-aminopyrazole-4-carboxylates
T2 - Selective synthesis of substituted 5-aza-9-deaza-adenines1
AU - Lim, Felicia Phei Lin
AU - Halcovitch, Nathan R.
AU - Tiekink, Edward R.T.
AU - Dolzhenko, Anton V.
N1 - 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
PY - 2018/4/12
Y1 - 2018/4/12
N2 - 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.
AB - 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.
KW - Pyrazole
KW - Triazine
KW - Purine isostere
KW - Pyrazolo[1,5-a][1,3,5]triazine
KW - Multicomponent reaction
KW - Dynamic NMR spectroscopy
U2 - 10.1016/j.tet.2018.02.054
DO - 10.1016/j.tet.2018.02.054
M3 - Journal article
VL - 74
SP - 1868
EP - 1879
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 15
ER -