L-Proline-catalyzed synthesis of novel 5-(1H-indol-3-yl-methylene)thiazolidine-2,4-dione derivatives as potential antihyperglycemic agents was written by Riyaz, S.;Naidu, A.;Dubey, P. K.. And the article was included in Synthetic Communications in 2011.Quality Control of 3-Methylthiazolidine-2,4-dione This article mentions the following:
Knoevenagel condensation between indole-3-carboxaldehyde (I) and an active methylene group containing 2,4-thiazolidinedione (II) in refluxing toluene using L-proline as a catalyst yielded 5-(1H-indol-3-yl-methylene)thiazolidine-2,4-dione, which on alkylation using 2 equiv of alkylating agent under phase-transfer-catalyzed (PTC) conditions using K2CO3 as a base in DMF gave N,NI-sym. disubstituted 5-(1H-indol-3-ylmethylene)-thiazolidine-2,4-diones. Alternately, the target compounds could be synthesized by condensation of N-alkyl-2,4-thiazolidinediones with 1-alkyl/phenylsulfonylindole-3-carboxaldehydes in a single step. Using this synthetic strategy, N,NI-unsym. disubstituted derivatives were prepared either by condensing I with N-substituted-2,4-thiazolidinediones to obtain 3-alkyl-5-(1H-indol-3-yl-methylene)thiazolidine-2,4-diones followed by alkylation under PTC conditions or condensing 1-alkyl/phenylsulfonylindole-3-carboxaldehydes with II to yield 5-(1-alkyl/phenylsulfonyl-1H-indol-3-yl-methylene)thiazolidine-2,4-diones followed by alkylation under PTC conditions. The latter are the dehydro analogs of the dihydro-N-substituted-5-(1H-indol-3-yl-methylene)-thiazolidine-2,4-diones, which are potential antihyperglycemic agents. In the experiment, the researchers used many compounds, for example, 3-Methylthiazolidine-2,4-dione (cas: 16312-21-3Quality Control of 3-Methylthiazolidine-2,4-dione).
3-Methylthiazolidine-2,4-dione (cas: 16312-21-3) belongs to thiazolidine derivatives. Thiazolidine derivatives have been found to exhibit very prominent anti-inflammatory and anti-nociceptive activity. Open-chain compounds are obtained when thiazolidines are treated with tris(trimethylsilyl)silane in a reaction in which the thiazolidine derivatives act as a source of α-aminoalkyl radicals.Quality Control of 3-Methylthiazolidine-2,4-dione
Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com