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An Alternative Regioselective Approach for the Synthesis of Highly Functionalized Derivatives of Pyrazolo[5,1‐ b ]purine Scaffold
Author(s) -
SheikhiMohammareh Seddigheh,
Shiri Ali
Publication year - 2018
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3242
Subject(s) - chemistry , regioselectivity , thiourea , annulation , pyrimidine , alkylation , purine , reagent , structural isomer , stereochemistry , nuclear magnetic resonance spectroscopy , combinatorial chemistry , two dimensional nuclear magnetic resonance spectroscopy , pyrazine , organic chemistry , catalysis , enzyme
A straightforward approach for the regioselective synthesis of highly functionalized pyrazolo[5,1‐ b ]purine from the annulation of 6‐bromo‐3‐cyano‐2‐(ethylthio)‐5‐methyl‐7‐oxo‐6,7‐dihydropyrazolo[1,5‐ a ]pyrimidine with thiourea as a bisnucleophilic reagent under reflux condition in CH 3 CN in the presence of Et 3 N has been developed. The N ‐alkylation of the synthesis compound was also accomplished. The true regioisomer was determined by 2 D‐NOESY NMR spectroscopy, as well.