1048915-76-9Relevant articles and documents
The thermal amidation of carboxylic acids revisited
Goossen, Lukas J.,Ohlmann, Dominik M.,Lange, Paul P.
, p. 160 - 164 (2009)
Factors affecting the thermal condensation of carboxylic acids with amines have been investigated, and an effective protocol for this waste-minimized, environmentally benign transformation has been identified. Fourteen examples demonstrate the applicability of this procedure to aliphatic, aromatic and heteroaromatic carboxylic acids and primary and secondary aliphatic as well as aromatic amines. The approach leads to the corresponding amides in good yields. Georg Thieme Verlag Stuttgart.
2,2-Diazido-1,2-diarylethanones: Synthesis and Reactivity with Primary Amines
Holzschneider, Kristina,H?ring, Andreas P.,Kirsch, Stefan F.
, p. 2824 - 2831 (2019/04/30)
We describe the synthesis and reactivity of a new class of diazidated compounds: the 2,2-diazido-1,2-diarylethanones. The diazides are easily accessible from 1,2-diarylethanones through a mild and simple protocol for the direct oxidative diazidation, using iodine and sodium azide in DMSO at room temperature. In studies towards their reactivity with amine nucleophiles under basic conditions, the diazides are shown to undergo a controlled fragmentation reaction that provides a straightforward access to the corresponding amides. In stark contrast to our previous results on the amine-triggered fragmentation of diazidated compounds, aromatic nitriles are found to be by-products of synthetic value. The net reaction consisting of diazidation and subsequent fragmentation, thus, provides a simple way to convert 1,2-diarylethanones into both aromatic amides and nitriles.
Pathways in the Degradation of Geminal Diazides
Holzschneider, Kristina,H?ring, Andreas P.,Haack, Alexander,Corey, Daniel J.,Benter, Thorsten,Kirsch, Stefan F.
, p. 8242 - 8250 (2017/08/14)
The degradation of geminal diazides is described. We show that diazido acetates are converted into tetrazoles through the treatment with bases. The reaction of dichloro ketones with azide anions provides acyl azides, through in situ formation of diazido ketones. We present experimental and theoretical evidence that both fragmentations may involve the generation of acyl cyanide intermediates. The controlled degradation of terminal alkynes into amides (by loss of one carbon) or ureas (by loss of two carbons) is also shown.
