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Microwave-assisted synthesis of pyrazolo[3,4-b]pyridine-spirocycloalkanediones by three-component reaction of 5-aminopyrazole derivatives, paraformaldehyde and cyclic β-diketones

✍ Scribed by Jairo Quiroga; Jorge Trilleras; Dayana Pantoja; Rodrigo Abonía; Braulio Insuasty; Manuel Nogueras; Justo Cobo

Book ID
104098046
Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
338 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

New pyrazolo [3,4-b]pyridine-5-spirocycloalkanedione derivatives were prepared via three-component reaction between 5-(4-R-benzylamino)pyrazoles, cyclic b-diketones and paraformaldehyde. The use of indandione as b-diketone resulted in the formation of two products, the pyrazolo[3,4-b]pyridine-5-spiroindanediones and 3-tert-butyl-1-phenylindeno[2,3-e]pyrazolo [3,4-b]pyridine. The structures of the pyrazolo [3,4-b]pyridine-5-spirocycloalkanedione were confirmed by single-crystal X-ray diffraction. This protocol provides a simple one-step synthetic methodology with the advantages of easy work-up, mild reaction conditions and environmentally benign.

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## Abstract magnified image 5‐Chloroethylpyrazolo[3,4‐__b__]pyridines were synthesized by condensation of 5‐aminopyrazoles with α‐acetyl γ‐butyrolactone followed by cyclization treating with phosphorous oxychloride. 5‐Chloroethyl‐pyrazolo[3,4‐__b__]pyridines, thus obtained, were then converted to