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 - http://www.scopus.com/inward/record.url?scp=85084220780&partnerID=8YFLogxK
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 -