Sulfonyl Group Dance: A Tool for the Synthesis of 6-Azido-2-sulfonylpurine Derivatives.,The Journal of Organic Chemistry

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Sulfonyl Group Dance: A Tool for the Synthesis of 6-Azido-2-sulfonylpurine Derivatives.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-03-13 , DOI: 10.1021/acs.joc.9b03518
Janis Miķelis Zaķis ₁ , Kristers Ozols ₁ , Irina Novosjolova ₁ , Reinis Vilšķērsts _{2,

3} , Anatoly Mishnev ₃ , Maris Turks ₁

Affiliation

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.

中文翻译：

磺酰基基团舞蹈：合成6-叠氮基-2-磺酰基嘌呤衍生物的工具。

当用叠氮化钠处理时，用9-取代的2-氯-6-磺酰基嘌呤可提供61-83％产率的6-叠氮基-2-磺酰基嘌呤衍生物。在优化的反应条件下，以一锅法获得标题化合物，该过程涉及用选定的亚磺酸钠和叠氮化钠依次处理2,6-二氯嘌呤。磺酰基基团的跳动（官能团交换）是由SNAr反应级联产生的，叠氮基甲亚胺-四唑（叠氮化物-四唑）互变异构平衡促进了这种反应。作为四唑嘌呤互变异构体的迈森海默型中间体的形成受到包括15N NMR在内的各种光谱方法的支持。

更新日期：2020-03-16

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