Reactions of polyfluorocarbonyl compounds with 1,3,3-trimethyl-3,4-dihydroisoquinoline and its derivatives

Reactions of fused pyrrole-2,3-diones with binucleophiles

“…42 In its tautomeric form, 1-methylen-1,2,3,4-tetrahydroisoquinoline contains an enamino fragment with two nucleophilic groups, and is promising targets for research. …”

Synthesis and some heterocyclization reactions of new diethyl (1,1-difluoro-3,3-dicyano-2-trifluoromethylallyl)phosphonate and ethyl 3,3-dicyano-2-[(diethoxyphosphoryl)difluoromethyl]acrylate

“…Alkylation is accompanied by heterocyclization to give 6,7-dihydro-2H-pyrido[2,1-a]isoquinolines 12a-d (48 h at room temperature, Scheme 7, Table 1). Obviously, the highly reactive enamine form is in equilibrium with the basic imine form and undergoes alkylation [15]. Attempts to effect such a transformation with ethyl 3,3-dicyano-2-[(diethoxyphosphoryl)difluoromethyl]acrylate were not successful.…”

“…General procedure for preparation of [(2-amino-3-cyano-6-methyl-1-aryl-4-trifluoromethyl-1,4-dihydropyridin-4-yl)-difluoromethyl]-phosphonic acid diethyl esters (13) and 3-cyano-4-[(diethoxyphosphoryl)difluoromethyl]-6-methyl-2-arylamino-1,4-dihydropyridine-4-carboxylic acid ethyl esters (15) Alkene 4 or 5 (0.2 g, 0.6 mmol) was added with stirring to a solution of the corresponding aniline (0.6 mmol) and acetone (100 mg, 1.7 mmol) in 8 ml of abs. CH 3 Cl and the mixture was kept at RT for 48 h. The crude product was purified by flash chromatography on a silica gel (chloroform-ethylacetate, 2:1).…”

Acid-Promoted Oxygen-Atom Transfer from a Novel Dihydroisoquinoline-Derived Oxaziridine Substituted at Position 1

“…Preparation of Imine 6 [25] To a cooled (0 C) solution of phosphoric acid H 2 SO 4 (95%) was added dropwise 1.1 ml of CH 3 CN in 20 ml of hexane under magnetic stirring. Then, tertiary …”