Synthetic utility of a heterocyclic o-aminoaldehyde: synthesis of pyrazolopyridopyrimidines, pyrazolonaphthyridines, and pyrazolopyrimidonaphthyridinones

A series of various polysubstituted pyrazolo[3,4- h ][1,6]naphthyridines, benzo[ b ]pyrazolo[3,4- h ][1,6]naphthyridines, and pyrazolo[4′,3′:5,6]pyrido[4,3- d ]pyrimidines were synthesized by Friedländer condensation of 4-amino-3-methyl-1-phenyl-1 H -pyrazolo[3,4- b ]pyridine-5-carbaldehyde ( o -ami...

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Bibliographic Details
Published in:Monatshefte für Chemie 2011-02, Vol.142 (2), p.169-175
Main Authors: Bagul, Sandeep M., Birari, Dilip R., Ghagare, Maruti G., Toche, Raghunath B., Jachak, Madhukar N.
Format: Article
Language:English
Subjects:
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Theoretical and Computational Chemistry
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Summary:A series of various polysubstituted pyrazolo[3,4- h ][1,6]naphthyridines, benzo[ b ]pyrazolo[3,4- h ][1,6]naphthyridines, and pyrazolo[4′,3′:5,6]pyrido[4,3- d ]pyrimidines were synthesized by Friedländer condensation of 4-amino-3-methyl-1-phenyl-1 H -pyrazolo[3,4- b ]pyridine-5-carbaldehyde ( o -aminoaldehyde) with active methylene compounds. The o -aminoaldehyde was functionalized to o -aminonitrile and o -aminocarboxamide with malononitrile and cyanoacetamide, respectively, which on condensation with monosubstituted ureas and acetic anhydride, respectively, afforded pyrazolo[3,4- h ]pyrimido[4,5- b ][1,6]naphthyridines. Graphical abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-010-0443-9