Synthesis of Purine Analogues: Photocatalyst-Free Visible-Light-Enhanced Annulation Approach to Pyrazolo[1,5-a][1,3,5]triazine-2,4-diamines

被引：18

作者：

Guo, Wei ^{[1
]}

Xie, Zhen ^{[1
]}

Cai, Liuhuan ^{[1
]}

Liu, Gongping ^{[1
]}

Deng, Ling ^{[1
]}

Mei, Weijie ^{[1
]}

Zou, Xiaoying ^{[1
]}

Zhong, Yumei ^{[1
]}

Zhuo, Xiaoya ^{[1
]}

Zheng, Lvyin ^{[1
]}

Fan, Xiaolin ^{[1
]}

机构：

[1] Gannan Normal Univ, Key Lab Organopharmaceut Chem Jiangxi Prov, Ganzhou 341000, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 12期

基金：

中国国家自然科学基金;

关键词：

XANTHINE-OXIDASE INHIBITOR; SULFOXIDE-CONTAINING DRUG; STRUCTURE-BASED DESIGN; POTENT INHIBITORS; GENERAL-APPROACH; C-NUCLEOSIDE; IN-VIVO; BOF-4272; DERIVATIVES; PHARMACOKINETICS;

D O I：

10.1021/acs.joc.1c00783

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new photocatalyst-free visible-light-enhanced strategy for the synthesis of pyrazolo[1,5-a][1,3,5]triazine-2,4-diamines via the formation of electron donor-acceptor (EDA) complexes is reported. The in situ generated pyrazolthiourea intermediates from 1H-pyrazol-3-amines and isothiocyanates undergo formal [4 + 2] annulation with 1,1,3,3-tetramethylguanidines (TMG) to deliver the corresponding products involved in three C-N bond formations in a one-pot protocol. The formation of EDA complex from pyrazolthiourea and TMG is confirmed by UV-vis spectroscopy and H-1 NMR experiments. Moreover, this mild reaction proceeds in the absence of any external transition metals, oxidants, bases, and ligands. This efficient methodology for the synthesis of purine analogues pyrazolo[1,5-a][1,3,5]triazine-2,4-diamines provides potential synthetic applications in the field of drug research and development.

引用

页码：8365 / 8380

页数：16

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