Chemoselective cyclocondensation of α-acylacetamidines with 2-methylsulfanyl-4,6-dichloropyrimidine-5-carbaldehyde

A New Synthesis of 2-Aminoindoles and 6-Aminopyrrolo[3,2-d]pyrimidines from π-Deficient 1,2-Dihaloarenes and Geminal Enediamines

“…[3] Yield 525 mg (92%); viscous oil; 1 3-Amino-3-ethoxy-1-(pyrrolidin-1-yl)prop-2-en-1-one (1c). [2] Cyanoacetic acid ethyl ester (15.8 g, 0.14 mol) was added dropwise to pyrrolidine (9.94 g, 0.14 mol) being cooled in an ice bath and stirred. The reaction mixture was left overnight at room temperature, and then filtered, washed with hexane and air dried to give 3-oxo-3-(pyrrolidin-1yl)propanenitrile.…”

Reaction of 2,4-dinitrofluorobenzene with enediamines. synthesis of cinnolines

“…As we have shown previously, enediamines 1 can cyclocondense with aromatic electrophiles (aldehydes and esters) containing an active halogen atom in an ortho position to the electrophilic group to give condensed aminoazines [1][2][3]. The reaction occurs chemoselectively, the aromatic halogen atom being substituted by the carbon of the nucleophilic center of the enediamine and an amino group reacts with an exocyclic electrophilic group.…”

Pot, atom and step economic synthesis: a diversity-oriented approach to construct 2-substituted pyrrolo[2,1-f][1,2,4]triazin-4(3H)-ones

“…The unexpected pyridine derivative D17 was isolated in good yield (84%), and a pyridine ring formed instead of the pyrimidine ring. It was proposed that the 3-substituted chromenone most likely reacted with the enamine tautomer of ethyl 3-amino-3-iminopropanoate 15 in the presence of NaOAc. The structure of D17 was confirmed by X-ray crystallography (Fig.…”