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Reactions of Cyclic Pseudothioureas with Acetylenedicarboxylates
Author(s) -
Liu KangChien,
Tuan Julia Ying,
Shih BiJane
Publication year - 1977
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.197700011
Subject(s) - chemistry , thiourea , dimethyl acetylenedicarboxylate , ring (chemistry) , medicinal chemistry , carbon disulfide , disulfide bond , acetylenedicarboxylate , nucleophile , ethanol , diamine , organic chemistry , cycloaddition , catalysis , biochemistry
Treatment of aliphatic 1,2‐, 1,3‐ or aromatic o ‐diamine with carbon disulfide provided the corresponding cyclic pseudothioureas (IIb‐j). Heating thiourea (IIa) or these compounds with dimethyl or diethyl acetylenedicarboxylate (IIIa, b) in ethanol resulted a nucleophilic addition of the sulfhydryl group to the C≡C bond accompanied with a ring‐closure condensation. Thus a series of alkoxycarbo‐methylidene derivatives of 2‐imino‐4‐thiazolidinone (IVa), imidazolo‐, benzimidazo‐and tetrahydropyrimido (2, 1‐b)‐3‐thiazolidinones (IVb‐k) was produced. An orientating experiment of saponifying the ester function of these compounds has also been carried out.