112142-59-3Relevant academic research and scientific papers
3-(Dimethylamino)-2,2-dimethyl-2H-azirine as an α-Aminoisobutyric-Acid (Aib) Equivalent: Cyclic Depsipeptides via Direct Amide Cyclization
Obrecht, Daniel,Heimgartner, Heinz
, p. 329 - 338 (2007/10/02)
In MeCN at room temperature, 3-(dimethylamino)-2,2-dimethyl-2H-azirine (1) and α-hydroxycarboxylic acids react to give diamides of type 8.Selective cleavage of the terminal N,N-dimethylcarboxamide group in MeCN/H2O leads to the corresponding carboxylic acids 13.In toluene/PhSH, phenyl thioesters of type 11 are formed.Starting with diamides 8, the formation of morpholin-2,5-diones 10 has been achieved either by direct amide cyclization via intermediate 1,3-oxazol-5(4H)-ones 9 or via base-catalyzed cyclization of the phenyl thioesters 11.Reaction of carboxylic acids with 1, followed by selective amide hydrolysis, has been used for the construction of peptides from α-hydroxy carboxylic acids and repetitive α-aminoisobutyric-acid (Aib) units.Cyclization of 14a, 17a, and 20a with HCl in toluene at 100 deg C gave the 9-, 12-, and 15-membered cyclic depsipeptides 15, 18, and 21, respectively.
3-DIMETHYLAMINO-2,2-DIMETHYL-2H-AZIRIN ALS Aib-AEQUIVALENT BEI HETEROCYCLENSYNTHESEN; SYNTHESE VON 6-, 9-, 12- UND 15-GLIEDRIGEN RINGEN
Obrecht, Daniel,Heimgartner, Heinz
, p. 1921 - 1924 (2007/10/02)
The cyclization reaction of the dimethylamides 2b, 5, 6 and 7, resulting from the reaction of mandelic acid with the aminoazirine 1, yields the 6-, 9-, 12- and 15-membered cyclic depsipeptides 10 - 13, respectively.
