L-Proline Catalyzed Synthesis of Novel 5-{[2-(2-phenylpiperazin-1-yl)quinolin] methylene}-2,4-dione Derivatives

Author(s): S.S. Praveen Kumar Darsi, K. Shiva Kumar, B. Rama Devi, A. Naidu, P.K. Dubey

Journal Name: Letters in Organic Chemistry

Volume 11 , Issue 8 , 2014

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Graphical Abstract:


L-proline is found to be an efficient catalyst for the Knoevenagel condensation of 2-chloroquinoline-3- carboxaldehyde 1a-c with an active methylene compound i.e., 2,4-thazolidinedione 2 in IPA affording novel substituted olefins 3a-c. The latter products reacted with N-substituted-3-phenylpiperazine 4a-c in the presence of KF in DMF to afford the corresponding 5-{[2-(2-phenylpiperazin-1-yl)quinolin]methylene}-2,4-dione derivatives 6a-i. Alternatively, 6ai were also synthesized from another reaction sequence 1 → 5 → 6. The structures of the synthesized compounds have been established on the basis of spectral and analytical data.

Keywords: 2-chloroquinoline-3-carboxaldehyde, 2, 4-thazolidinedione, L-proline, Knoevenagel condensation, N-substituted-3- phenylpiperazine.

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Article Details

Year: 2014
Published on: 12 June, 2014
Page: [551 - 555]
Pages: 5
DOI: 10.2174/1570178611999140404113821
Price: $65

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