42436-22-6Relevant academic research and scientific papers
Synthesis, photochemical and luminescent properties of ortho-hydroxystyrylquinazolinone-linked benzocrown ethers
Ovchinnikova, Irina G.,Kim, Grigory A.,Matochkina, Eugene G.,Kodess, Mikhail I.,Slepukhin, Pavel A.,Kovalev, Igor S.,Nosova, Emilia V.,Rusinov, Gennady L.,Charushin, Valery N.
, p. 16 - 28 (2018)
Photoinduced transformations of (E)-2-(2-hydroxystyryl)quinazolinone-linked benzo[15(18)]crown-5(6) ethers in solutions have been studied by using UV–vis absorption and NMR spectroscopy. These crown ethers were found to have dual emission at 520 and 650 nm, associated with proton-transfer tautomer emission (ESIPT-luminescence) as a rare case of excited-state proton-transfer reaction in the non-pseudocyclic chromophoric systems. It was established also, that the organic bases affect the luminescence intensity of solutions of these compounds in the 550–650-nm wavelength range. An X-ray crystallography analysis of molecular structures of crown ethers and their complexes in crystals has been carried out. The fact of reversible photo/thermal E-Z isomerization in DMF and Et3N for these macroheterocyclic compounds has been confirmed. An opportunity to control the photochemical isomerization rate of quinazolinone 2-(hydroxyphenyl)ethenyl derivatives by changing pH of the medium has been demonstrated.
Pericyclic reactions in the synthesis of new 5-aryl-5,6-dihydroquinolino[2,1-b]quinazolin-12-ones
Ovchinnikova, Irina G.,Kim, Grigory A.,Matochkina, Eugeniya G.,Kodess, Mikhail I.,Nosova, Emiliya V.,Rusinov, Gennady L.,Charushin, Valery N.
, p. 135 - 137 (2019)
Novel tetracyclic 5-aryl-5,6-dihydroquinolino[2,1-b]quinazolin-12-ones bearing benzo-15-crown-5 ether and dimethoxyphenyl moieties were prepared by one-pot cascade synthesis involving the thermally allowed pericyclic transformations of (E)-2-(2-methoxystyryl)quinazolinones. The pseudocyclic transition state of six-electron electrocyclization has been located and the activation barrier has been estimated by RHF/3-21G and 6-311G* calculation methods. The crystal structure of N-[4-(2,3-dimethoxy-12-oxo-5,6-dihydroquinolino[2,1-b]quinazolin-5-yl)-3-methoxyphenyl]acetamide was determined by X-ray diffraction analysis.
Synthesis of some substituted 4(3H) quinazolinones of diverse biological activities
Abu-Shady,Michael,Abbas,Abu-Youssef
experimental part, p. 313 - 336 (2009/10/10)
THE SYNTHESIS of 3-(3-hydroxy-4-methoxyphenyl) and 3-(4-hydroxy-2- methylphenyl)-4(3H)-quinazolinone and their nitroanalogs 2 and 3 is described. Reaction of 2 and 3 with alkyl halides gave the alkoxy derivatives 4 and 7 , reaction with alkyl or aryl isocyanates afforded the alkyl or aryl carbamoyloxy derivatives 5 and 8 , while reaction with aldehydes yielded the 2-styryl derivatives 6 and 9. Refluxing 3 with secondary amines and formaldehyde produced mannich bases 10. Reaction of 3 with ethyl chloroacetate gave the ethyl phenoxyacetate 11 which upon refluxing with hydrazine hydrate yielded the acid hydrazide 12. Further reaction of 12 with aldehydes or isothiocyanates afforded the hydrazones 13 or the thiosemicarbazides 14, respectively. Cyclization of the latter with chloroacetic acid produced the thiazolidinones 15. Fifteen of the newly synthesized compounds were screened for tranquillizing , anticonvulsant and analgesic activities. Twelve of the tested compounds showed marked activities.
