NDLI: Catalyst-free Biginelli-type synthesis of new functionalized 4,7-dihydropyrazolo[1,5-a]pyrimidines

Content Provider	Semantic Scholar
Author	Kolosov, Maksim A. Beloborodov, Dmitriy A. Orlov, Valeriy D. Dotsenko, Victor V.
Copyright Year	2016
Abstract	The Biginelli-type reaction of 5-amino-3-arylpyrazole-4-carbonitriles with aldehydes and 1,3-dicarbonyl compounds was studied in detail. We found that the reaction requires no catalysts and proceeds in boiling DMF to give 2-aryl-6-RC(O)-4,7-dihydropyrazolo[1,5-a]pyrimidin-3-carbonitriles in good yields. The reaction of aminopyrazoles with dicarbonyls leading to 6-unsubstituted pyrazolo[1,5-a]pyrimidines proceeds competitively and becomes the dominant process under acid-promoted conditions. 2-Aryl-8-oxo-4,5,6,7,8,9-hexahydropyrazolo[5,1-b]quinazolin-3-carbonitriles were obtained under catalyst-free conditions in up to 80% yields starting from 5-amino-3-arylpyrazole-4-carbonitriles, aldehydes and 1,3-cyclohexanedione.
Starting Page	7573
Ending Page	7579
Page Count	7
File Format	PDF HTM / HTML
DOI	10.1039/C6NJ00336B
Volume Number	40
Alternate Webpage(s)	http://www.rsc.org/suppdata/c6/nj/c6nj00336b/c6nj00336b1.pdf
Alternate Webpage(s)	https://pubs.rsc.org/en/content/articlepdf/2016/nj/c6nj00336b
Alternate Webpage(s)	https://doi.org/10.1039/C6NJ00336B
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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