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Synthesis of 5‐cyanopyrazolo[3,4‐ b ]pyridines in the reaction of 5‐amino‐3‐methyl‐1‐phenylpyrazole with arylidene derivatives of malonodinitrile and ethyl cyanoacetate
Author(s) -
Quiroga Jairo,
Alvarado Mario,
Insuasty Braulio,
Moreno Rodolfo,
Raviña Enrique,
Estevez Isabel,
De Almeida S. Regina H.
Publication year - 1999
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.5570360533
Subject(s) - chemistry , ethyl cyanoacetate , aryl , carbon 13 nmr , stereochemistry , medicinal chemistry , organic chemistry , malononitrile , catalysis , alkyl
This paper describes the synthesis of a new series of 6‐amino‐4‐aryl‐5‐cyanopyrazolo[3,4‐ b ]pyridines 4 and 4‐aryl‐5‐cyano‐6 H ‐pyrazolo[3,4‐ b ]pyridin‐6‐ones 5 from the reaction of 5‐amino‐3‐methyl‐1‐phenylpyrazole 1 with arylidene derivatives of malonodinitrile 2 and ethyl cyanoacetate 3 . The structure of the final compounds was determined on the basis of nmr measurements, especially by 1 H, 1 H‐, 1 H, 13 C‐COSY, DEPT and X‐ray diffraction.