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One-Pot, Pseudo-Five-Component Synthesis of Bis[2-(arylimino)-1,3-thiazolidin-4-ones]

✍ Scribed by Abdolali Alizadeh; Zohreh Noaparast; Hamideh Sabahno; Nasrin Zohreh

Publisher
John Wiley and Sons
Year
2010
Tongue
German
Weight
137 KB
Volume
93
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Synthesis and characterization of bis[2‐(arylimino)‐1,3‐thiazolidin‐4‐ones] are described. The one‐pot, pseudo‐five‐component reaction of an aliphatic diamine, isothiocyanatobenzene, and dialkyl but‐2‐ynedioate at room temperature in anhydrous CH~2~Cl~2~ gives the title compound in relatively high yield. Under the same conditions, aromatic 1,2‐diamines yield 2‐(arylimino)‐N‐(enaminoaryl)‐1,3‐thiazolidin‐4‐ones in a pseudo‐four‐component reaction. Their structures were corroborated spectroscopically (IR, ^1^H‐ and ^13^C‐NMR, and EI‐MS) and by elemental analyses. A plausible mechanism for this type of cyclization is proposed (Scheme 3).

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