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

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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; Halcovitch, Nathan R.; Tiekink, Edward R.T. et al.
In: Tetrahedron, Vol. 74, No. 15, 12.04.2018, p. 1868-1879.

Research output: Contribution to Journal/MagazineJournal articlepeer-review

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Lim FPL, Halcovitch NR, Tiekink ERT, Dolzhenko AV. A new microwave-assisted, three-component reaction of 5-aminopyrazole-4-carboxylates: Selective synthesis of substituted 5-aza-9-deaza-adenines1. Tetrahedron. 2018 Apr 12;74(15):1868-1879. Epub 2018 Feb 27. doi: 10.1016/j.tet.2018.02.054

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Bibtex

@article{833c74a8f39543788580a82ed185d8ff,
title = "A new microwave-assisted, three-component reaction of 5-aminopyrazole-4-carboxylates: Selective synthesis of substituted 5-aza-9-deaza-adenines1",
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, Pyrazolo[1,5-a][1,3,5]triazine, Multicomponent reaction, Dynamic NMR spectroscopy",
author = "Lim, {Felicia Phei Lin} and Halcovitch, {Nathan R.} and Tiekink, {Edward R.T.} and Dolzhenko, {Anton V.}",
note = "This is the author{\textquoteright}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",
year = "2018",
month = apr,
day = "12",
doi = "10.1016/j.tet.2018.02.054",
language = "English",
volume = "74",
pages = "1868--1879",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "15",

}

RIS

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 -