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

Alizadeh Abdolali | Zendy; Noaparast Zohreh | Zendy; Sabahno Hamideh | Zendy; Zohreh Nasrin | Zendy

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

Author(s) -

Alizadeh Abdolali,

Noaparast Zohreh,

Sabahno Hamideh,

Zohreh Nasrin

Publication year - 2010

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.200900402

Subject(s) - chemistry , yield (engineering) , anhydrous , component (thermodynamics) , elemental analysis , diamine , molar ratio , medicinal chemistry , proton nmr , organic chemistry , stereochemistry , catalysis , materials science , physics , metallurgy , thermodynamics

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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