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

Felicia Phei Lin Lim; Nathan R. Halcovitch; Edward R.T. Tiekink; Anton V. Dolzhenko

doi:10.1016/j.tet.2018.02.054

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

Felicia Phei Lin Lim, Nathan R. Halcovitch, Edward R.T. Tiekink, Anton V. Dolzhenko

Malaysia Sch of Pharmacy

Research output: Contribution to journal › Article › Research › peer-review

20 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1868-1879
Number of pages	12
Journal	Tetrahedron
Volume	74
Issue number	15
DOIs	https://doi.org/10.1016/j.tet.2018.02.054
Publication status	Published - 12 Apr 2018

Keywords

Dynamic NMR spectroscopy
Multicomponent reaction
Purine isostere
Pyrazole
Pyrazolo[1,5-a][1,3,5]triazine
Triazine

Access to Document

10.1016/j.tet.2018.02.054

Cite this

@article{38b9b3aa773b4e86a8510fee2ec1d7fc,

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

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 = "Dynamic NMR spectroscopy, Multicomponent reaction, Purine isostere, Pyrazole, Pyrazolo[1,5-a][1,3,5]triazine, Triazine",

author = "Lim, {Felicia Phei Lin} and Halcovitch, {Nathan R.} and Tiekink, {Edward R.T.} and Dolzhenko, {Anton V.}",

note = "Funding Information: This work is supported by the Ministry of Higher Education, Malaysia under Fundamental Research Grant Scheme (FRGS). We would like to thank Nexus Analytics Sdn. Bhd. and Anton Paar Malaysia Sdn. Bhd. for their technical support. Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd Copyright: Copyright 2018 Elsevier B.V., All rights reserved.",

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",

number = "15",

}

TY - JOUR

T1 - A new microwave-assisted, three-component reaction of 5-aminopyrazole-4-carboxylates

T2 - Selective synthesis of substituted 5-aza-9-deaza-adenines

AU - Lim, Felicia Phei Lin

AU - Halcovitch, Nathan R.

AU - Tiekink, Edward R.T.

AU - Dolzhenko, Anton V.

N1 - Funding Information: This work is supported by the Ministry of Higher Education, Malaysia under Fundamental Research Grant Scheme (FRGS). We would like to thank Nexus Analytics Sdn. Bhd. and Anton Paar Malaysia Sdn. Bhd. for their technical support. Publisher Copyright: © 2018 Elsevier Ltd Copyright: Copyright 2018 Elsevier B.V., All rights reserved.

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 - Dynamic NMR spectroscopy

KW - Multicomponent reaction

KW - Purine isostere

KW - Pyrazole

KW - Pyrazolo[1,5-a][1,3,5]triazine

KW - Triazine

UR - http://www.scopus.com/inward/record.url?scp=85042928193&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2018.02.054

DO - 10.1016/j.tet.2018.02.054

M3 - Article

AN - SCOPUS:85042928193

SN - 0040-4020

VL - 74

SP - 1868

EP - 1879

JO - Tetrahedron

JF - Tetrahedron

IS - 15

ER -

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

Abstract

Keywords

Access to Document

Other files and links

Cite this