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IJC-B Vol.51B(09) [September 2012] >


Title: PEG-600 mediated one-pot synthesis of quinolinylidinethiazolidine-2,4-diones as potential anti-hyperglycemic agents
Authors: Riyaz, Sd
Naidu, A
Dubey, P K
Keywords: PEG-600
Knoevenagel condensation
Quinoline-2-aldehyde
2,4-thiazolidinedione
C=C reduction
Mg/EtOH
Issue Date: Sep-2012
Publisher: NISCAIR-CSIR, India
Abstract: Knoevenagel condensation between quinoline-2-aldehyde 1 and active methylene group containing 2,4-thia­zolidinedione (TZD) 2 in PEG-600 at 100°C for 2 hr, without the usage of any base, yields 5-quinolin-2-ylmethylene-thiazolidine-2,4-dione 3 which on alkylation gives N-substituted-5-quinolin-2-ylmethylene-thiazolidine-2,4-diones 5. Alternatively, 5 can also be synthesized by condensing N-substituted-thiazolidine-2,4-dione 4 with 1 in PEG-600 at 100°C. It is possible to prepare 5 directly by condensing 2 with 1 followed by alkylation under one-pot conditions. The α,β-unsaturated carbonyl derivatives 5, thus obtained, are subjected to C=C reduction using magnesium turnings in refluxing ethanol to obtain the corresponding reduced products 6 in high yields which are novel potential anti-hyperglycemic agents.
Page(s): 1396-1399
CC License:  CC Attribution-Noncommercial-No Derivative Works 2.5 India
ISSN: 0975-0983(Online); 0376-4699(Print)
Source:IJC-B Vol.51B(09) [September 2012]

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