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

Wei Guo, Zhen Xie, Liuhuan Cai, Gongping Liu, Ling Deng, Weijie Mei, Xiaoying Zou, Yumei Zhong, Xiaoya Zhuo, Lvyin Zheng, Xiaolin Fan

The Journal of organic chemistry 2021 Jun 18

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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 1H 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.

Citation

Wei Guo, Zhen Xie, Liuhuan Cai, Gongping Liu, Ling Deng, Weijie Mei, Xiaoying Zou, Yumei Zhong, Xiaoya Zhuo, Lvyin Zheng, Xiaolin Fan. Synthesis of Purine Analogues: Photocatalyst-Free Visible-Light-Enhanced Annulation Approach to Pyrazolo[1,5-a][1,3,5]triazine-2,4-diamines. The Journal of organic chemistry. 2021 Jun 18;86(12):8365-8380