Reactions of Some Pyrazole-3-Carboxylic Acids and Carboxylic Acid Chlorides with Various O- and N- Nucleophiles

Author(s): Ilhan Ozer Ilhan, Ayse Caglayan, Zulbiye Onal, Senem Akkoc, Mehmet Cadır.

Journal Name: Letters in Organic Chemistry

Volume 10 , Issue 8 , 2013

Become EABM
Become Reviewer

Abstract:

The 1H–pyrazole-3-carboxylic acid 2 and its remarkably stable acid chlorides 3 can easily be converted into the corresponding carbohydrazide, ester or amide derivatives 4, 6 and 7, respectively, from reaction with alcohols or Nnucleophiles. The acid chloride (3) was also converted easily into the new derivatives consisting of 5-phenyl-1H-pyrazole 8a,b. The cyclocondensation reactions of 2 with some hydrazines led to the formation of pyrazolo[3,4-d ]pyradizinone 5 derivative. The nitrile derivative 9 was obtained by dehydration of 7a,b in a mixture of SOCl2 and DMF. The thermal decomposition of 4-Benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid 2b leads to the formation of [1-(4- nitrophenyl)-5-phenyl-1H-pyrazole-4-yl] phenylmethanone 10) It has been demonstrated that with the variation in reaction conditions, the reaction changes and leads to different products. The structures of these newly synthesized compounds were determined from the FT-IR, 1H and 13C NMR spectroscopic data and elemental analyses.

Keywords: 2, 3-Furandione, Pyrazole-3-carboxylic acid, Cyclic oxalyl compounds, Pyrazole-3-carboxylic acid chloride, Pyrazolo[ 3, 4-d]pyridazinones.

Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 10
ISSUE: 8
Year: 2013
Page: [602 - 610]
Pages: 9
DOI: 10.2174/15701786113109990025
Price: $65

Article Metrics

PDF: 9