Reactions of 3-benzoyl-7-dimethylamino-4-hydroxycoumarin and their potential applications in solution- and solid-phase synthesis.
3-Benzoyl-7-dimethylamino-4-hydroxycoumarin was synthesized and its UV-vis spectra in various mixtures of MeOH and CH(2)Cl(2) were measured. The diketone lactone exists mainly in the exocyclic-enol form in protic solvents and the endocyclic-enol form in nonpolar solvents. Acetylation, amination and methylation products of the diketone lactone were characterized by X-ray crystallography. The results indicated that acetylation of coumarin-based diketone lactones occurs exclusively at the 4-hydroxy group, but that amination takes place specifically at the C-3 carbonyl group. Among the prepared compounds, amination products were found to exhibit photochromic property and colorimetric ion-sensing ability, and methylation product has the potential to function as a primary amine protection group.
Kuo
Pei-Yu
PY
Department of Chemistry, Tunghai University, 181, Taichung-Kang Rd. Sec.3, Taichung, 407, Taiwan.
Chuang
Rong-Ren
RR
Yang
Ding-Yah
DY
D015110:4-Hydroxycoumarins / Q000737:chemistry*; D000107:Acetylation; D000586:Amination; D000588:Amines / Q000737:chemistry; D018360:Crystallography, X-Ray; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D008670:Metals / Q000032:analysis; D008745:Methylation; D012996:Solutions; D012997:Solvents / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013379:Substrate Specificity
C542229:3-benzoyl-7-dimethylamino-4-hydroxycoumarin; D015110:4-Hydroxycoumarins; D000588:Amines; D007783:Lactones; D008670:Metals; D012996:Solutions; D012997:Solvents; C068805:4-hydroxycoumarin