Sulfonyl Group Dance: A Tool for the Synthesis of 6-Azido-2-sulfonylpurine Derivatives

Jānis Miķelis Zaķis; Kristers Ozols; Irina Novosjolova; Reinis Vilšķērsts; Anatoly Mishnev; Māris Turks

doi:10.1021/acs.joc.9b03518

Sulfonyl Group Dance: A Tool for the Synthesis of 6-Azido-2-sulfonylpurine Derivatives

Jānis Miķelis Zaķis
, Kristers Ozols
, Irina Novosjolova
, Reinis Vilšķērsts
, Anatoly Mishnev
, Māris Turks^*

^*Corresponding author for this work

Faculty of Pharmacy

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

17 Citations (Scopus)

Abstract

9-Substituted 2-chloro-6-sulfonylpurines provide 6-azido-2-sulfonylpurine derivatives with 61-83% yields when treated with sodium azide. Under optimized reaction conditions, the title compounds are obtained in a one-pot process, which involves a sequential treatment of 2,6-dichloropurines with a selected sodium sulfinate and sodium azide. Such a sulfonyl group dance (functional group swap) results from a cascade of S_NAr reactions, which are facilitated by azidoazomethine-tetrazole (azide-tetrazole) tautomeric equilibrium. The formation of Meisenheimer-type intermediates as tetrazolopurine tautomers was supported by various spectroscopic methods, including ¹⁵N NMR.

Original language	English
Pages (from-to)	4753-4771
Number of pages	19
Journal	Journal of Organic Chemistry
Volume	85
Issue number	7
DOIs	https://doi.org/10.1021/acs.joc.9b03518
Publication status	Published - 3 Apr 2020

Field of Science

3.1 Basic medicine
1.4 Chemical sciences

Publication Type*

1.1. Scientific article indexed in Web of Science and/or Scopus database

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.9b03518

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@article{55cb11c0bbce48fdb3f2023a919e654e,

title = "Sulfonyl Group Dance: A Tool for the Synthesis of 6-Azido-2-sulfonylpurine Derivatives",

abstract = "9-Substituted 2-chloro-6-sulfonylpurines provide 6-azido-2-sulfonylpurine derivatives with 61-83\% yields when treated with sodium azide. Under optimized reaction conditions, the title compounds are obtained in a one-pot process, which involves a sequential treatment of 2,6-dichloropurines with a selected sodium sulfinate and sodium azide. Such a sulfonyl group dance (functional group swap) results from a cascade of SNAr reactions, which are facilitated by azidoazomethine-tetrazole (azide-tetrazole) tautomeric equilibrium. The formation of Meisenheimer-type intermediates as tetrazolopurine tautomers was supported by various spectroscopic methods, including 15N NMR.",

author = "Zaķis, \{Jānis Miķelis\} and Kristers Ozols and Irina Novosjolova and Reinis Vil{\v s}ķērsts and Anatoly Mishnev and Māris Turks",

note = "Funding Information: The authors thank the Latvian Council of Science grant LZP-2018/2-0037 for financial support and Dr. chem. Krist i ne Lazdovi{\v c}a for IR and UV analysis. Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",

year = "2020",

month = apr,

day = "3",

doi = "10.1021/acs.joc.9b03518",

language = "English",

volume = "85",

pages = "4753--4771",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Sulfonyl Group Dance

T2 - A Tool for the Synthesis of 6-Azido-2-sulfonylpurine Derivatives

AU - Zaķis, Jānis Miķelis

AU - Ozols, Kristers

AU - Novosjolova, Irina

AU - Vilšķērsts, Reinis

AU - Mishnev, Anatoly

AU - Turks, Māris

N1 - Funding Information: The authors thank the Latvian Council of Science grant LZP-2018/2-0037 for financial support and Dr. chem. Krist i ne Lazdoviča for IR and UV analysis. Publisher Copyright: Copyright © 2020 American Chemical Society. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2020/4/3

Y1 - 2020/4/3

N2 - 9-Substituted 2-chloro-6-sulfonylpurines provide 6-azido-2-sulfonylpurine derivatives with 61-83% yields when treated with sodium azide. Under optimized reaction conditions, the title compounds are obtained in a one-pot process, which involves a sequential treatment of 2,6-dichloropurines with a selected sodium sulfinate and sodium azide. Such a sulfonyl group dance (functional group swap) results from a cascade of SNAr reactions, which are facilitated by azidoazomethine-tetrazole (azide-tetrazole) tautomeric equilibrium. The formation of Meisenheimer-type intermediates as tetrazolopurine tautomers was supported by various spectroscopic methods, including 15N NMR.

AB - 9-Substituted 2-chloro-6-sulfonylpurines provide 6-azido-2-sulfonylpurine derivatives with 61-83% yields when treated with sodium azide. Under optimized reaction conditions, the title compounds are obtained in a one-pot process, which involves a sequential treatment of 2,6-dichloropurines with a selected sodium sulfinate and sodium azide. Such a sulfonyl group dance (functional group swap) results from a cascade of SNAr reactions, which are facilitated by azidoazomethine-tetrazole (azide-tetrazole) tautomeric equilibrium. The formation of Meisenheimer-type intermediates as tetrazolopurine tautomers was supported by various spectroscopic methods, including 15N NMR.

UR - https://www.scopus.com/pages/publications/85084220780

U2 - 10.1021/acs.joc.9b03518

DO - 10.1021/acs.joc.9b03518

M3 - Article

C2 - 32150410

AN - SCOPUS:85084220780

SN - 0022-3263

VL - 85

SP - 4753

EP - 4771

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 7

ER -

Sulfonyl Group Dance: A Tool for the Synthesis of 6-Azido-2-sulfonylpurine Derivatives

Abstract

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