1,2,3-Triazoles as leaving groups in SNAr–Arbuzov reactions: synthesis of C6-phosphonated purine derivatives

1,2,3-Triazoles as leaving groups in SNAr–Arbuzov reactions: synthesis of C6-phosphonated purine derivatives

A new method for C–N bond transformations into C–P bonds was developed using 1,2,3-triazoles as leaving groups in SNAr–Arbuzov reactions. A series of C6-phosphonated 2-triazolylpurine derivatives was synthesized for the first time, with the isolated yields reaching up to 82% in the C–P-bond-forming...

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Main Authors: Kārlis-Ēriks Kriķis, Irina Novosjolova, Anatoly Mishnev, Māris Turks
Format: Article
Language:English
Published: Beilstein-Institut 2021-01-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
arbuzov reaction
2,6-bistriazolylpurines
nucleophilic aromatic substitution
purinylphosphonates
Online Access:https://doi.org/10.3762/bjoc.17.19
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spelling doaj-da7560335d834bd8bef91fea45440db62021-02-08T09:47:07ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-01-0117119320210.3762/bjoc.17.191860-5397-17-191,2,3-Triazoles as leaving groups in SNAr–Arbuzov reactions: synthesis of C6-phosphonated purine derivativesKārlis-Ēriks Kriķis0Irina Novosjolova1Anatoly Mishnev2Māris Turks3Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaFaculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaLatvian Institute of Organic Synthesis, Aizkraukles Str. 21, LV-1006, Riga, LatviaFaculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaA new method for C–N bond transformations into C–P bonds was developed using 1,2,3-triazoles as leaving groups in SNAr–Arbuzov reactions. A series of C6-phosphonated 2-triazolylpurine derivatives was synthesized for the first time, with the isolated yields reaching up to 82% in the C–P-bond-forming event. The SNAr–Arbuzov reaction of 2,6-bistriazolylpurines follows the general regioselectivity pattern of the C6-position being more reactive towards substitution, which was unambiguously proved by X-ray analysis of diethyl (9-heptyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)-9H-purin-6-yl)phosphonate.https://doi.org/10.3762/bjoc.17.19arbuzov reaction2,6-bistriazolylpurinesnucleophilic aromatic substitutionpurinylphosphonates
collection DOAJ
language English
format Article
sources DOAJ
author Kārlis-Ēriks Kriķis
Irina Novosjolova
Anatoly Mishnev
Māris Turks
spellingShingle Kārlis-Ēriks Kriķis
Irina Novosjolova
Anatoly Mishnev
Māris Turks
1,2,3-Triazoles as leaving groups in SNAr–Arbuzov reactions: synthesis of C6-phosphonated purine derivatives
Beilstein Journal of Organic Chemistry
arbuzov reaction
2,6-bistriazolylpurines
nucleophilic aromatic substitution
purinylphosphonates
author_facet Kārlis-Ēriks Kriķis
Irina Novosjolova
Anatoly Mishnev
Māris Turks
author_sort Kārlis-Ēriks Kriķis
title 1,2,3-Triazoles as leaving groups in SNAr–Arbuzov reactions: synthesis of C6-phosphonated purine derivatives
title_short 1,2,3-Triazoles as leaving groups in SNAr–Arbuzov reactions: synthesis of C6-phosphonated purine derivatives
title_full 1,2,3-Triazoles as leaving groups in SNAr–Arbuzov reactions: synthesis of C6-phosphonated purine derivatives
title_fullStr 1,2,3-Triazoles as leaving groups in SNAr–Arbuzov reactions: synthesis of C6-phosphonated purine derivatives
title_full_unstemmed 1,2,3-Triazoles as leaving groups in SNAr–Arbuzov reactions: synthesis of C6-phosphonated purine derivatives
title_sort 1,2,3-triazoles as leaving groups in snar–arbuzov reactions: synthesis of c6-phosphonated purine derivatives
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2021-01-01
description A new method for C–N bond transformations into C–P bonds was developed using 1,2,3-triazoles as leaving groups in SNAr–Arbuzov reactions. A series of C6-phosphonated 2-triazolylpurine derivatives was synthesized for the first time, with the isolated yields reaching up to 82% in the C–P-bond-forming event. The SNAr–Arbuzov reaction of 2,6-bistriazolylpurines follows the general regioselectivity pattern of the C6-position being more reactive towards substitution, which was unambiguously proved by X-ray analysis of diethyl (9-heptyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)-9H-purin-6-yl)phosphonate.
topic arbuzov reaction
2,6-bistriazolylpurines
nucleophilic aromatic substitution
purinylphosphonates
url https://doi.org/10.3762/bjoc.17.19
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