One‐Pot,Pseudo‐Five‐Component Synthesis of Bis[2‐(arylimino)‐1,3‐thiazolidin‐4‐ones] |
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| Authors: | Abdolali Alizadeh Zohreh Noaparast Hamideh Sabahno Nasrin Zohreh |
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| Institution: | 1. Department of Chemistry, Tarbiat Modares University, P.O. Box 14115‐175, Tehran, Iran, (phone: +98‐21‐88006631;2. fax: +98‐21‐88006544) |
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| Abstract: | Synthesis and characterization of bis2‐(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 CH2Cl2 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, 1H‐ and 13C‐NMR, and EI‐MS) and by elemental analyses. A plausible mechanism for this type of cyclization is proposed (Scheme 3). |
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| Keywords: | Multicomponent reactions 1 3‐Thiazolidin‐4‐ones Amines aliphatic Isothiocyanatobenzene But‐2‐ynedioate dialkyl Benzene‐1 2‐diamines |
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