94475-59-9Relevant academic research and scientific papers
A CONVENIENT METHOD FOR THE SYNTHESIS OF αβ-UNSATURATED CARBOXYLIC ACID AMIDES UTILIZING A NEW HETERO-BIFUNCTIONAL REAGENT, DMPATT
Nagao, Yoshimitsu,Hagiwara, Yuichi,Yamada, Shozo,Ochiai, Masahito,Fujita, Eiichi
, p. 4686 - 4689 (2007/10/02)
As a new extention of monitored aminolysis of 3-acyl-1,3-thiazolidine-2-thione(ATT), a convenient procedure for the synthesis of αβ-unsaturated carboxylic acid amides has been developed using a new hetero-bifunctional reagent, 3-dimethylphosphonoacetyl-1,3-thiazolidine-2-thione (DMPATT).DMPATT was effectively used as the bridging reagent between amino (or imino) compounds and aldehydes (or ketone) to afford various olefinic amides in good yields.KEYWORDS - thiazolidine-2-thione; hetero-bifunctional reagent; αβ-unsaturated amide; Wittig reaction; ferulyltryptamine
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
MONITORED AMINOLYSIS OF 3-ACYLTHIAZOLIDINE-2-THIONE : A NEW CONVENIENT SYNTHESIS OF AMIDE
Nagao, Yoshimitsu,Seno, Kaoru,Kawabata, Kohji,Miyasaka, Tadayo,Takao, Sachiko,Fujita, Eiichi
, p. 841 - 844 (2007/10/02)
3-Acylthiazolidine-2-thiones (1) were easily prepared and they were treated with several amines in dichloromethane to give amides 4 in very high yields within a short time.Aminoalcohols and aminophenols were selectively converted into acylaminoalcohols and acylaminophenols, respectively, by this reaction.One can monitor the reaction by disappearance of the yellow color of the starting material 1.Some amide alkaloids (15-18) have effectively been synthesized.
