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

Abstract

A water mediated and thiamine hydrochloride catalysed eco-compatible efficient method was developed for the synthesis of spiro[acenaphthylene-1,2 0 [1,3]-thiazolidine]-2,4 0 (1H)-diones via multi-component reaction of acenaphthylene-1,2-dione, substituted anilines, and a-mercaptocarboxylic acid at 80°C temperature. This transformation involves the formation of two C-N bonds and one C-S bond leading to the creation of a five-member ring in a one-pot operation. Easy availability and recovery of the catalyst, no toxic/organic solvents, and high yield of product make the protocol attractive, sustainable, and economic. Graphical AbstractO O NH 2 1 2 HS O OH 3 O N S O R 1 R 1 R R R 1 = H, CH 3

Contemporary progress in the green synthesis of spiro-thiazolidines and their medicinal significance: a review

“…R. Singh and colleagues 48 described a water-facilitated and thiamine hydrochloride promoted efficient and eco-compatible process for the production of spiro[acenaphthylene-1,2'[1,3]-thiazolidine]-2,4′(1 H )-diones (27) via MCR of substituted anilines, α -mercaptocarboxylic acid, and acenaphthylene-1,2-dione at 80 °C ( Scheme 7 ). One C–S bond and two C–N bonds were formed during this conversion, which resulted in the one-pot assembly of a five-membered ring.…”

Recent Advances of Thiamine in Organic Synthesis

“…[66] In 2017, Singh and Ganaie prepared a series of spiro[acenaphthylene-1,2'[1,3]-thiazolidine]-2,40 (1H)-diones from anilines, acenaphthylene-1,2-dione and α-mercaptocarboxylic acid via VB 1 -catalyzed three-component reaction (Scheme 30). [67] In this transformation, a five-membered ring containing nitrogen and sulfur atoms was constructed via the formation of one CÀ S bond and two CÀ N bonds. Advantageously for this reaction, the catalytic system could be recycled three times without loss in activity (from 90% to 87% of yield).…”

Recent Advances in the Synthesis of Hetero- and Carbocyclic Compounds­ and Complexes Based on Acenaphthylene-1,2-dione

“…The significant advantages reported for this methodology are easy handling and recoverability of the catalyst. 72…”