Styrylbenzodiazinones 2. Chromo- et fluoroionophores dérivés du monoaza-15-couronne-5. Synthèse et structure

Abstract

In connection with our work on styryl derivatives of benzodiazinones, we have prepared the 7-N,N-dimethylamino-3-methyl-1,4-benzodiazin-2-one 4a and two chromo- and fluoroionophores derived from the monoaza-15-crown-5 and styrylbenzodiazinones. A structural study of these compounds by 1H and 13C NMR, UV spectrophotometry, and molecular modelling was carried out. Unlike styrylbenzoxazinones, styrylbenzodiazinone derivatives showed a Z/E isomerization in acetonitrile solution. The isomerization was photoinduced, was catalysed by metallic ions, and was a reversible process. As well, an efficient alkylation reaction of the lactam function of benzodiazinones is described.

Quinoxalin‐2(1H)‐ones: Chemical Synthesis, Fluorescence Properties and Applications

“…Quinoxalin‐2(1 H )‐ones are nitrogenated counterparts of 2 H ‐benzopyran‐2‐one (coumarins). Comparative analysis of spectral data of quinoxalin‐2(1 H )‐one, N ‐methyl‐2‐quinoxalin‐2(1H)‐one, and 2‐methoxyquinoxaline carried out by Dogra, confirmed that quinoxalin‐2(1 H )‐one predominantly exists as a cyclic amide rather than a 2‐hydroxyquinoxaline (or imidic acid), thus are structurally closer to coumarins [41] …”

“…In 1993, Cazaux reported that 3‐( p ‐aminostyryl)‐quinoxalin‐2(1 H )‐ones exhibited E/Z isomerization in the presence of cations (such as Ca 2+ or Zn 2+ ) in ACN (Scheme 29). [41] This isomerization process was investigated by following the optical density change at the maximum absorption wavelength in the presence of small amount of metallic cations after 1 h. Moreover, after irradiation by white light for 10 min, the optical density returned to its initial state. When this solution was subsequently placed in the dark, the optical density reached the same plateau than that was obtained after the addition of cationic metals.…”

“…Comparative analysis of spectral data of quinoxalin-2(1H)-one, N-methyl-2-quinoxalin-2(1H)-one, and 2-methoxyquinoxaline carried out by Dogra, confirmed that quinoxalin-2(1H)-one predominantly exists as a cyclic amide rather than a 2-hydroxyquinoxaline (or imidic acid), thus are structurally closer to coumarins. [41] Despite this structural similarity, photophysical properties of quinoxalin-2(1H)-ones are, however, far less reported than those of coumarins, and less used in subsequent fluorescence applications. Table 1 compares their photophysical properties in terms of absorption, emission and fluorescence quantum yield.…”

Synthesis and structure of styryl-substituted azines

“…It was shown recently that quinoline derivatives are promising substrates for the photoinduced electrocyclic reaction [3]. The synthetic potential of these phototransformations is suffi ciently wide and makes it possible to use them for the synthesis of new polyfused heteroaromatic compounds (Scheme 1).π-Conjugated organic compounds based on aromatic systems attract signifi cant attention with respect to the application as semiconductors in organic fi eld transistors (OFETs), organic light-emitting diodes (OLEDs), and photogalvanic batteries, and also as biological active compounds, e.g., potential antitumor agents [4].It is known [5][6][7][8][9][10][11][12] that the main procedure for the synthesis of styrylheterocycles is the aldol-type condensation of methyl derivatives of heterocyclic bases with benzaldehyde derivatives. The primary conditions of the condensation contained the use of relatively strong protic acids and bases, and the range of the possible reaction products was limited.…”

“…It is known [5][6][7][8][9][10][11][12] that the main procedure for the synthesis of styrylheterocycles is the aldol-type condensation of methyl derivatives of heterocyclic bases with benzaldehyde derivatives. The primary conditions of the condensation contained the use of relatively strong protic acids and bases, and the range of the possible reaction products was limited.…”