Metal-involving generation of aminoheterocycles from N-substituted cyanamides: Toward sustainable chemistry (a Minireview)

作者: Dmitrii S Bolotin , Valentin A Rassadin , Nadezhda A Bokach , Vadim Yu Kukushkin , None

DOI: 10.1016/J.ICA.2016.02.025

关键词: Green chemistryReaction conditionsChemistry1,3-Dipolar cycloadditionOrganic chemistryMetalCycloadditionCyanamideNucleophilic addition

摘要: Abstract This review is focused on progress in the area of metal-involving reactions cyanamides leading to aminosubstituted heterocycles. The consideration covers metal-mediated cyanamide–amidoxime coupling giving 5-aminosubstituted 1,2,4-oxadiazoles and cycloaddition nitrones or azides cyanamide species furnishing 2,3-dihydro-1,2,4-oxadiazoles 5-aminotetrazoles, respectively. Gold-catalyzed heterocyclization acetylenes providing 2-aminooxazole systems also considered. All these reaction schemes are discussed from viewpoints sustainable processes with particular focus how application organic transformations provides milder conditions, increase yields target products, reduce number steps thus making chemistry more environmentally benign.

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