Synthesis of 1,3‐thiazole and 1,2,4‐oxadiazole substituted spiro[3H‐indole‐3,2′‐thiazolidine]‐2,4′(1H)‐diones

Abstract

Some new derivatives of spiro[3H‐indole‐3,2′‐thiazolidine]‐2,4′(1H)‐dione with the heterocyclic ring such as substituted thiazole and 1,2,4‐oxadiazole attached to the indolinone ring via CH2 linkage has been synthesized in moderate yields. The synthesis have been carried out by making use of the reactivity of the NH group of the indolinone moiety present in spiro[3H‐indole‐3,2′‐thiazolidine]‐2,4′(1H)‐dione.

An eco-compatible synthesis of novel spiro[acenaphthylene-1,2′[1,3]-thiazolidine]-2,4′(1H)-diones using thiamine hydrochloride as efficient catalyst in aqueous medium

“…A literature survey reveals various reports on synthesis of spiro-indole thiazolidinones [47][48][49][50][51][52][53], but to the best of our knowledge there is no report on the synthesis of spiro compounds by incorporating acenapthaquinone and 4-thiazolidinone rings together. Hence, inspired by these findings and in continuation of our ongoing work to develop environmentally benign methodologies [54][55][56][57][58][59][60][61] for the synthesis of biologically useful heterocycles, we have investigated a threecomponent protocol for the synthesis of drug-like spiro[acenaphthylene-1,2 0 [1,3]-thiazolidine]-2,4 0 (1H)-diones from the multi-component reaction of acenapthaquinone, substituted anilines, and a-mercaptoacetic acid in good yield using thiamine hydrochloride as a green, inexpensive, and reusable catalyst in aqueous medium.…”

An Efficient One-Pot Synthesis of 3-Aryl-5-(Dialkoxymethyl)-1,2,4-Oxadiazoles under Solvent-Free Conditions

“…1). [13][14][15][16][17][18][19] Treatment of 2,2-diethoxypropionamide and dimethylacetamide dimethyl acetal gave N- [1-(dimethylamino) ethylidene]-2,2-dimethoxypropanamide which upon reaction with hydroxylamine followed by treatment with acetic acid produced 5-(1,1-diethoxyethyl)-3-methyl-1,2,4-oxadiazole (3a, Fig. 1).…”