Synthesis, IR, UV/vis-, (1)H NMR and DFT study of chelatophore functionalized 1,3-benzoxazinone spiropyrans.
Six novel functionalized spiropyran's derivatives of 2H-1,3-benzoxazinone series were synthesized by introducing the substituents with chelating ability into 2H-chromene part of the 8'-formyl-7'-hydroxy-3-methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazine-2-spiro-2'-[2H]-chromene (I) by condensation with 2-aminophenol, 2-amino-4-methylphenol, 2-amino-4-nitrophenol, 2-amino-1-methylbenzimidazole, 4-amino-4H-1,2,4-triazole, N-(4-aminophenyl)acetamide. (1)H NMR, UV/vis, IR spectroscopy combined with quantum-chemical calculations employing density functional theory (DFT) were used to study their structure. All substances, except 2-amino-4-nitrophenol derivative exist in solid state and in solution solely in closed spiroform, while the mentioned one undergoes partial spiropyran ring opening. In DMSO solution NMR spectra show ratio of 2:1 of closed and opened form, correspondingly.
Department of Chemistry, Southern Federal University, 7, Zorge Street, Rostov-on-Don 344019, Russian Federation.
Antony O
AO
Bulanov
Leonid D
LD
Popov
Igor N
IN
Shcherbakov
Victor A
VA
Kogan
Valerii A
VA
Barachevsky
Vladimir V
VV
Lukov
S N
SN
Borisenko
Yu N
YN
Tkachenko
D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry*; D002614:Chelating Agents / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry*; D011789:Quantum Theory; D013053:Spectrophotometry; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013816:Thermodynamics
D001578:Benzopyrans; D002614:Chelating Agents; D007211:Indoles; D009574:Nitro Compounds; D010078:Oxazines; C088184:spiropyran