Naslov
Mechanochemical and Conformational Study of N- heterocyclic Carbonyl-Oxime Transformations

Autori
Primožič, Ines ; Hrenar, Tomica ; Baumann, Krešimir ; Krišto, Lucija ; Križić, Ivana ; Tomić, Srđanka

Izvornik
Croatica chemica acta (0011-1643) 87 (2014), 2; 155-162

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
nitrogen heterocycles; oximes; mechanochemical synthesis; conformational analysis; DFT

Sažetak
New mechanochemical pathways for the transformation of six N-heterocyclic carbonyl compounds into oximes using hydroxylamine hydrochloride were explored. Reactions were performed first without any base since the heterocyclic moieties (imidazole, benzimidazole, pyridine and quinuclidine) have an intrinsic basic nitrogen atom. This green, solvent free method was suitable for all compounds (up to quantitative yields) except for N-benzyl substituted imidazole and benzimidazole-2-carbaldehyde. For the slower reacting aldehydes, reactions with liquid assisted grinding and addition of sodium hydroxide were performed as well. Conformational analysis and quantum-chemical calculations revealed steric and electronic reasons for the lower reactivity of N-benzyl substituted derivatives.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA