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A convenient route for the synthesis of pyrazolo[3,4-d]pyrimidine, pyrazolo[3,4-b][1,6]naphthyridine and pyrazolo[3,4-b]quinoline derivatives

✍ Scribed by Madhukar N. Jachak; Appasaheb B. Avhale; Vijay J. Medhane; Raghunath B. Toche

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
363 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

Friedländer condensation of 5-aminopyrazole-4-carbaldehydes 1 with formamide 2a or benzamide 2b gave pyrazolo [3,4-d]pyrimidine derivatives 3. Cyclocondensation of 1 with cyclopentanone, N-benzyl-4piperidone and 6-methoxy-1-tetralone yielded cyclopenta[b]pyrazolo[4,3-e]pyridines 4, pyrazolo[3,4-b]-[1,6]naphthyridines 5 and benzo[h]pyrazolo[3,4-b]quinolines 6, respectively. Analogous condensation of cyclohexanone 7a or 2-methyl-1-cyclohexanone 7b with 1 afforded pyrazolo[3,4-b]quinoline derivatives 8a-d. Heating 1 with dimedone furnished pyrazolo[3,4-b]quinolinone derivatives 9. Vilsmeier-Haack formylation of 9 yielded a mixture of two compounds 10 and 11. Further bispyrazolo[3,4-b:4,3-f]quinolines 12a, b were obtained on cyclocondensation of 11a, b with phenyl hydrazine.

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