15249-82-8Relevant academic research and scientific papers
Aqueous-phase synthesis of 2-aminothiazole and 2-iminothiazolidine derivatives catalyzed by diammonium hydrogen phosphate and DABCO
Balalaie, Saeed,Nikoo, Sahar,Haddadi, Shokat
, p. 2521 - 2528 (2008/12/22)
2-Aminothiazole and 2-iminothiazolidine derivatives were synthesized from the reaction of phenacyl bromide, thiourea, and its derivatives in aqueous media catalyzed by diammonium hydrogen phosphate (10%) and DABCO (10%) at room temperature in an efficient and simple procedure. Copyright Taylor & Francis Group, LLC.
Condensation of (2-Bromo-1-phenylethylidene)malononitrile with Substituted Thioureas: An Unusual Ring Size Effect
Svetlik, Jan,Turecek, Frantisek,Goljer, Igor
, p. 4740 - 4744 (2007/10/02)
Condensations of the title electrophile with ambient S,N-nucleophiles, e.g., thiourea, N,N'-diphenylthiourea, and thiosemicarbazide, proceed via initial S-alkylation followed by closure of the thiazole ring.In contrast to this, cyclic thioureas with the five-, six- and seven-membered rings afford distinct condensation products depending on the size of the ring. 2-Imidazolinethione gave 7-cyano-2,3-dihydro-5-mercapto-6-phenyl-1H-pyrrolo-imidazole in low yield. 3,4,5,6-Tetrahydro-2(1H)-pyrimidinethione afforded malonitrile in high yield, while 1,3,4,5,6,7-hexahydro-2H-1,3-diazepine-2-thione gave 7-amino-8-cyano-9-phenyl-2,3,4,5-tetrahydropyridodiazepine in moderate yield.A common feature of these cyclizations is the primary S-nucleophilic attack, which was confirmed by isolation and characterization of the corresponding intermediates.The effects of ring size are discussed.
Reactions of N,N-Dialkyl-N'-arylthioureas with α-Haloketones and of 2-Substituted Imino-1,3-oxathioles with Heterocumulenes
Singh, Harjit,Ahuja, A. S.,Malhotra, N.
, p. 1019 - 1022 (2007/10/02)
N,N-Dialkyl-N'-arylthioureas react with phenacyl halides to give 2-arylimino-5-phenyl-1,3-oxathioles (I), 3-aryl-2-arylimino-4-phenyl-4-thiazolines (III), aryl isothiocyanates and N,N'-diarylthioureas.I reacts with heterocumulenes like phenyl isocyanate and phenyl isothiocyanate to give 3,4-diaryl-2-arylimino-4-thiazolines, N,N'-diarylthioureas, arylacetylenes and COS or CO2.Mechanisms of formation of the various products have been proposed, based on TLC monitoring at regular time intervals.These are independently supported by chemical reactions.
