Harnessing Amino Acids as Dual Synthons: I₂-DMSO/FeCl3-Promoted [3+2+1] Cyclization
for Pyrazolo[3,4-d]pyrimidine Synthesis
Yu-Man Song
1
State Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent
Biosensor Technology and Health, Central China Normal University School of Chemistry,
Wuhan, China (Ringgold ID: RIN428680)
,
Ting Chen
2
State Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent
Biosensor Technology and Health, College of Chemistry, Central China Normal University
School of Chemistry, Wuhan, China (Ringgold ID: RIN428680)
,
Li-Sheng Wang
1
State Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent
Biosensor Technology and Health, Central China Normal University School of Chemistry,
Wuhan, China (Ringgold ID: RIN428680)
,
You Zhou
1
State Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent
Biosensor Technology and Health, Central China Normal University School of Chemistry,
Wuhan, China (Ringgold ID: RIN428680)
,
Yongxing Tang
3
National Key Laboratory of Green Pesticide, International Joint Research Center for
Intelligent Biosensor Technology and Health, College of Chemistry, Central China Normal
University, Wuhan, China (Ringgold ID: RIN12446)
,
Chun-Yan Wu
1
State Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent
Biosensor Technology and Health, Central China Normal University School of Chemistry,
Wuhan, China (Ringgold ID: RIN428680)
,
Yan-Dong Wu
1
State Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent
Biosensor Technology and Health, Central China Normal University School of Chemistry,
Wuhan, China (Ringgold ID: RIN428680)
,
Jia-Chen Xiang
4
School of Chemistry and Chemical Engineering, Southeast University, Nanjing, China (Ringgold ID: RIN12579)
,
Anxin Wu
5
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, Central China
Normal University School of Chemistry, Wuhan, China (Ringgold ID: RIN428680)
› Institutsangaben Gefördert durch:
Southeast University's “Zhi-Shan Young Scholars of Excellence” Support Program
2242025RCB0021
Gefördert durch:
Jiangsu Province Youth Science and Technology Talent Support Project
JSTJ-2024-454
Gefördert durch:
National Natural Science Foundation of China
22171098,22301035
The synthesis of pyrazolopyrimidine has attracted considerable attention since its
nitrogen-atom-rich bicyclic backbone exhibits diverse bioactivities. We report a facile
and straightforward synthesis of 4,6-disubstituted pyrazolo[3,4-d]pyrimidine from
α-amino acids and 5-aminopyrazole. This unprecedented transformation is enabled by
I2-DMSO reagent combination and facilitated by FeCl3. A domino sequence involving
I₂-mediated Strecker degradation of amino acids followed by [3+2+1] cyclization is
proposed as the reaction mechanism. Two electronically distinct intermediates derived
from amino acid fragmentation act as C1N1 and C1 synthons, respectively, and concurrently
participate in the pyrimidine ring cyclization.
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