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

ISSN: 1875-6255 (Online)
ISSN: 1570-1786 (Print)


Volume 11, 10 Issues, 2014


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Letters in Organic Chemistry

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Universidad de Alicante Apdo
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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 and P.K. Dubey

Affiliation: Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad College of Engineering, Kukatpally, Hyderabad (A.P), India-500 085.

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

Volume: 11
Issue Number: 8
First Page: 551
Last Page: 555
Page Count: 5
DOI: 10.2174/1570178611999140404113821
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