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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
C=C reduction
Issue Date: Sep-2012
Publisher: NISCAIR-CSIR, India
Abstract: Knoevenagel condensation between quinoline-2-aldehyde <b style="mso-bidi-font-weight:normal">1</b> and active methylene group containing 2,4-thia­zolidinedione (TZD) <b style="mso-bidi-font-weight:normal">2</b> in PEG-600 at 100°C for 2 hr, without the usage of any base, yields 5-quinolin-2-ylmethylene-thiazolidine-2,4-dione <b style="mso-bidi-font-weight:normal">3</b> which on alkylation gives N-substituted-5-quinolin-2-ylmethylene-thiazolidine-2,4-diones <b style="mso-bidi-font-weight:normal">5</b>. Alternatively, <b style="mso-bidi-font-weight:normal">5</b> can also be synthesized by condensing N-substituted-thiazolidine-2,4-dione <b style="mso-bidi-font-weight:normal">4</b> with <b style="mso-bidi-font-weight:normal">1</b> in PEG-600 at 100°C. It is possible to prepare <b style="mso-bidi-font-weight:normal">5</b> directly by condensing <b style="mso-bidi-font-weight:normal">2 </b>with <b style="mso-bidi-font-weight: normal">1 </b>followed by alkylation under one-pot conditions. The α,β-unsaturated carbonyl derivatives <b style="mso-bidi-font-weight:normal">5,</b> thus obtained, are subjected to C=C reduction using magnesium turnings in refluxing ethanol to obtain the corresponding reduced products <b style="mso-bidi-font-weight:normal">6</b> in high yields which are novel potential anti-hyperglycemic agents.
Description: 1396-1399
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.51B(09) [September 2012]

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