74058-73-4Relevant articles and documents
Monitored Aminolysis of 3-Acyl-1,3-thiazolidine-2-thiones: Synthesis of Amides and Amide Alkaloids
Nagao, Yoshimitsu,Seno, Kaoru,Kawabata, Kohji,Miyasaka, Tadao,Takao, Sachiko,Fujita, Eiichi
, p. 2687 - 2699 (2007/10/02)
A functional heterocycle, 3-acyl-1,3-thiazolidine-2-thione has been shown to be effective as an acylating reagent for the amino group.ATT (1) was readily prepared by several methods, and reacted with various amino compounds in CHCl3, CH2Cl2, THF, EtOH, THF-H2O, or sulfolane to afford the corresponding amides, 2a-w and 3-10 in very high yields within a short time.This reagent exhibits high chemo-selectivity.Its reaction with the diamines 13 and 15 and the triamine 29, which include a primary amino group(s) and a secondary amino group, gave the products acylated only at the primary amino group(s), 14, 16, and 30, respectively, in high yields.Aminoalcohols and aminophenols were chemoselectively converted into acylaminoalcohols and acylaminophenols, respectively, by ATT (1).By utilizing this method, several amide alkaloids (26, 28, 30, and 34) were efficiently synthesized.This new aminolysis can be monitored by the disappearance of the yellow color of the starting materials, ATT (1); it is remarkably characteristic of this reaction. Keywords - monitored aminolysis; 3-acyl-1,3-thiazolidine-2-thione; high chemo-selectivity; amide synthesis; fagaramide; dolicotheline; spermidine; maytenine; N-ferulyltryptamine
