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Synthesis of purines and adenines containing the hexafluoroisopropyl group

Several new derivatives of adenine, purine, and theophylline containing the (CF(3))(2)CH group connected to a nitrogen atom of the imidazole ring were prepared by the reaction of 2,2,4,4-tetrakis(trifluoromethyl)-1,3-dithietane (1) with the corresponding substrates, resulting in the selective alkyla...

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Autores principales: Petrov, Viacheslav, Dooley, Rebecca J, Marchione, Alexander A, Diaz, Elizabeth L, Clem, Brittany S, Marshall, William
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7670113/
https://www.ncbi.nlm.nih.gov/pubmed/33224300
http://dx.doi.org/10.3762/bjoc.16.224
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author Petrov, Viacheslav
Dooley, Rebecca J
Marchione, Alexander A
Diaz, Elizabeth L
Clem, Brittany S
Marshall, William
author_facet Petrov, Viacheslav
Dooley, Rebecca J
Marchione, Alexander A
Diaz, Elizabeth L
Clem, Brittany S
Marshall, William
author_sort Petrov, Viacheslav
collection PubMed
description Several new derivatives of adenine, purine, and theophylline containing the (CF(3))(2)CH group connected to a nitrogen atom of the imidazole ring were prepared by the reaction of 2,2,4,4-tetrakis(trifluoromethyl)-1,3-dithietane (1) with the corresponding substrates, resulting in the selective alkylation of one of the nitrogen atoms of the imidazole ring. The reaction proceeds under mild conditions in a polar solvent, giving the alkylated products in 47–78% yield. While for purine and 4- and 5-azabenzimidazole, the reaction led to a mixture of two isomers, the reaction of adenine and the corresponding 2-fluoro derivative was regioselective, resulting in the formation of only one isomer in each case. The alkylation of theophylline led to the formation of a new derivative of caffeine.
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spelling pubmed-76701132020-11-19 Synthesis of purines and adenines containing the hexafluoroisopropyl group Petrov, Viacheslav Dooley, Rebecca J Marchione, Alexander A Diaz, Elizabeth L Clem, Brittany S Marshall, William Beilstein J Org Chem Full Research Paper Several new derivatives of adenine, purine, and theophylline containing the (CF(3))(2)CH group connected to a nitrogen atom of the imidazole ring were prepared by the reaction of 2,2,4,4-tetrakis(trifluoromethyl)-1,3-dithietane (1) with the corresponding substrates, resulting in the selective alkylation of one of the nitrogen atoms of the imidazole ring. The reaction proceeds under mild conditions in a polar solvent, giving the alkylated products in 47–78% yield. While for purine and 4- and 5-azabenzimidazole, the reaction led to a mixture of two isomers, the reaction of adenine and the corresponding 2-fluoro derivative was regioselective, resulting in the formation of only one isomer in each case. The alkylation of theophylline led to the formation of a new derivative of caffeine. Beilstein-Institut 2020-11-11 /pmc/articles/PMC7670113/ /pubmed/33224300 http://dx.doi.org/10.3762/bjoc.16.224 Text en Copyright © 2020, Petrov et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Petrov, Viacheslav
Dooley, Rebecca J
Marchione, Alexander A
Diaz, Elizabeth L
Clem, Brittany S
Marshall, William
Synthesis of purines and adenines containing the hexafluoroisopropyl group
title Synthesis of purines and adenines containing the hexafluoroisopropyl group
title_full Synthesis of purines and adenines containing the hexafluoroisopropyl group
title_fullStr Synthesis of purines and adenines containing the hexafluoroisopropyl group
title_full_unstemmed Synthesis of purines and adenines containing the hexafluoroisopropyl group
title_short Synthesis of purines and adenines containing the hexafluoroisopropyl group
title_sort synthesis of purines and adenines containing the hexafluoroisopropyl group
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7670113/
https://www.ncbi.nlm.nih.gov/pubmed/33224300
http://dx.doi.org/10.3762/bjoc.16.224
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