Tandem amide coupling and hydroamination: unexpected benzotriazole oxide addition to the propiolic acid triple bond

Abstract

Amides are common molecules which are most often prepared using benzotriazole oxide coupling reagents. Such amides can be derivatised with compounds that contain a triple carbon-carbon bond in order to...

Structural Determination of the Hexacoordinated [Zn(L)2]2+ Complex Isomer Type Using Solution-State NMR, DFT Calculations and X-ray Crystallography

“…Transitions between two isomers of the same compound are expected to be less favorable than transitions between two conformers or rotamers, and separate signals of two isomers can be obtained in liquid-state NMR spectroscopy. Indeed, in our previous work we observed distinct Z and E isomers of one organic compound in liquid 1 H and 13 C NMR spectra [36]. In that work, a similar calculation procedure was used and experimental observation of two set of signals agreed with the observation in calculation procedure that transitions between E and Z isomers were not detected during meta-dynamics runs used for the generation of an ensemble of conformers.…”

Oxazoline amino acid bioconjugates: one-pot synthesis and analysis of supramolecular interactions

“…In the first attempt to synthesize the basic compound 3 m1 , the reaction was carried out with the commonly used benzotriazole reagents TBTU/HOBt (Scheme S1 and reaction 1, Table 1, ESI †). 35 However, analysis of the isolated products revealed only the bis-alanine compound 2 m1 , while compounds 3 m1 and 4 m1 were not detected. Instead, ester-amide byproducts 6 m1 , 7 m1 and 8 m1 formed in trace amounts (Scheme 1b).…”