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Synthesis and Structure of 3,4‐Dihydropyrido[2′,3′:3,4]pyrazolo[1,5‐ a ][1,3,5]triazin‐2‐amines [1][Dolzhenko, A. V., 2011]
Author(s) -
Dolzhenko Anton V.,
Bai Shiqi,
Dolzhenko Anna V.,
Chui Wai Keung
Publication year - 2012
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.851
Subject(s) - chemistry , synthon , tautomer , reagent , amine gas treating , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , medicinal chemistry , organic chemistry
A new convenient synthon for heterocyclic chemistry, namely 1 H ‐pyrazolo[3,4‐ b ]pyridin‐3‐ylguanidine was successfully prepared by selective guanylation of 1 H ‐pyrazolo[3,4‐ b ]pyridin‐3‐amine. A series of 3,4‐dihydropyrido[2′,3′:3,4]pyrazolo[1,5‐ a ][1,3,5]triazin‐2‐amines was synthesized from 1 H ‐pyrazolo[3,4‐ b ]pyridin‐3‐ylguanidine using aldehydes or ketones as one‐carbon inserting reagents. The tautomeric preferences of the products were determined using spectroscopic ( e.g ., 2D NOESY NMR) and single crystal X‐ray diffraction data.