The regioselectivity on a cyclic thioamide group towards different electrophiles was studied on the model compound 4-methyl-1-thioxo-1,2,4,5-tetrahydro[1,2,4]triazolo [4,3-a]quinazolin-5-one 1. The examined compound 1 reacts with alkyl halides, amines in the presence of formaldehyde, acyl halides and compounds having activated double bonds to afford the N-substituted derivatives 2, 3 and 6. The...

N-Hydroxysuccinimide (NHS) ester terminal groups are commonly used to covalently couple amine-containing biomolecules (e.g., proteins and peptides) to surfaces via amide linkages. This one-step aminolysis is often performed in buffered aqueous solutions near physiological pH (pH 6 to pH 9). Under these conditions, the hydrolysis of the ester group competes with the amidization process, potentia...

The present mechanistic study comprehensively explores alternative scenarios for activation of the amine-linked allene C=C linkage toward nucleophilic amido attack in the intramolecular hydroamination of a prototypical 1,3-disubstituted aminoallene by a well-characterised samarocene-amido catalyst. Firstly, the non-insertive mechanism by Scott featuring C-N ring closure with concomitant amino p...

We report the preparation of degradable polymer networks by conventional free radical copolymerization n-butyl acrylate with a crosslinker (1 mol %) and dibenzo[c,e]oxepane-5-thione (DOT) as strand-cleaving comonomer. Addition only 4 % DOT imparts synthesized full degradability aminolysis, whereas gels less (2–3 cannot be degraded. This data confirms recently proposed reverse gel-point model fo...