114877-91-7Relevant articles and documents
Synthesis of isothiocyanates using DMT/NMM/TsO? as a new desulfurization reagent
Janczewski, ?ukasz,Kolesińska, Beata,Kr?giel, Dorota
, (2021/05/29)
Thirty-three alkyl and aryl isothiocyanates, as well as isothiocyanate derivatives from esters of coded amino acids and from esters of unnatural amino acids (6-aminocaproic, 4-(aminomethyl)benzoic, and tranexamic acids), were synthesized with satisfactory or very good yields (25–97%). Synthesis was performed in a “one-pot”, two-step procedure, in the presence of organic base (Et3 N, DBU or NMM), and carbon disulfide via dithiocarbamates, with 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO? ) as a desulfurization reagent. For the synthesis of aliphatic and aromatic isothiocyanates, reactions were carried out in a microwave reactor, and selected alkyl isothiocyanates were also synthesized in aqueous medium with high yields (72–96%). Isothiocyanate derivatives of L-and D-amino acid methyl esters were synthesized, under conditions without microwave radiation assistance, with low racemization (er 99 > 1), and their absolute configuration was confirmed by circular dichroism. Isothiocyanate derivatives of natural and unnatural amino acids were evaluated for antibacterial activity on E. coli and S. aureus bacterial strains, where the most active was ITC 9e.
Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water
Fu, Zhicheng,Yuan, Wenhao,Chen, Ning,Yang, Zhanhui,Xu, Jiaxi
, p. 4484 - 4491 (2018/10/17)
We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates by the two procedures in satisfactory yields. Halogens, benzylic C-H bonds, methylthio, nitro, ester, alkenyl, electron-rich or -deficient (hetero)aryls, acetylenyl, and even phenolic and alcoholic hydroxyls are well tolerated. The one-pot procedure in water can also be used to realize the preparation of chiral isothiocyanates from chiral amines, and the modification of bioactive structures with free amino groups. In large-scale preparation, simple and practical purification procedures independent of column chromatography are developed.
A facile one-pot synthesis of selenoureidopeptides employing lialhseh through staudinger aza-wittig-type reaction
Sharanabai, Kupendra M.,Prabhu, Girish,Panduranga, Veladi,Sureshbabu, Vommina V.
, p. 801 - 806 (2015/03/14)
A one-pot protocol for the synthesis of selenoureidopeptides employing lithium aluminum hydride hydroselenide (LiAlHSeH) as a selenating agent via a Staudinger aza-Wittig-type reaction is reported. The protocol involves the use of Nα-protected aminoalkyl azides and isothicyanato esters to afford the desired products in good yields. This protocol is a direct approach to the synthesis of selenourea compounds that avoids the synthesis of isoselenocyanates and does not require multistep synthesis.
