New aspects of the chemistry of 2,3-dihydro-1H-1,5-benzodiazepine

Orlov, V. D.; Kolos, N. N.; Yaremenko, F. G.; Lavrushin, V. F.

doi:10.1007/bf00561358

Cited by 9 publications

(6 citation statements)

References 2 publications

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“…The dihydrobenzodiazepine structure was first suggested as the product of the cyclocondensation of mesityl oxide with orthophenylenediamine (Mushkalo, 1958). The chemistry of aromatic derivatives of 2,3-dihydro-1H-1,5-benzodiazepine began to be studied especially after 1970 (Nawojski et al, 1977;Yaremenko et al, 1979;Orlov et al, 1980). In 1983, it was found that the heptagonal cycle of benzodiazepines is decomposed into benzimidazole by heating in the presence of acids (Orlov et al, 1983), which suggested the impossibility of the formation of the heptagonal dihydrodiazepinic heterocycle reaction product of chalcones with orthophenylenediamine (1) (Zheliakov et al, 1972).…”

Section: Introductionmentioning

confidence: 99%

“…Benzodiazepine 7membered cycles are thermodynamically less stable than those of 5 and 6 members, especially if they are not aromatic. Only by 1997, it was demonstrated that the reaction of chalcones with ortho-phenylenediamine produces the benzodiazepine cycle (Nawojski and Nawrocka, 1977;Yaremenko et al, 1979. Orlov et al, 1980.…”

Section: Introductionmentioning

confidence: 99%

“…Dihydrobenzodiazepines were also detected in the reaction of some aliphatic unsaturated ketones (Kalyanam and Manjunatha, 1991;Kaspzyk and Kolinski, 1984). This cyclocondensation is carried out under mild conditions by base catalysis with a first step of amination of the β-enonic fragment followed by cyclocondensation (Orlov et al, 1980). Electrophilic substituents on the aromatic chalcone rings hinder the formation of the heptagonal heterocycle (Orlov et al, 1981).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 2,3-Dihydro-1h-1,5-Benzodiazepines Containing the 8- Hydroxyquinolinic Fragment

Marrugo-Gonzalez¹,

Orlov²,

Fernandez‐Maestre³

2016

PTQ

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Benzodiazepines are used as anxiolytic, hypnotic, sedative, and antidepressant drugs and to treat anxiety, insomnia, and epileptic seizures and show other types of biological activities. In this study, ten new 4(2)-(8-hydroxyquinolinil-5)-2(-4)-aryl-2,3-dihydro-1H-1,5-benzodiazepines and their rearrangement products, 2-substituted benzimidazoles, were synthesized from 1-aryl-3- (8-hydroxyquinolinil-5) propenone-1 (-3) and ophenylenediamine in methanol-triethylamine (1:1) solution. The reaction between the diamine and chalcones containing the 8-hydroxyquinoline fragment was carried out under mild conditions by base-catalysis amination of the β-enonic fragment of the chalcones followed by cyclo condensation. The structures of these compounds were studied by spectroscopic methods (IR and 1H-NMR) and their chelating properties were demonstrated. We calculated and discuss their theoretical biological activity and the influence of metal chelation on the electron acceptor hydroxyquinolinic fragment on the electronic spectra.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of 2,3-Dihydro-1h-1,5-Benzodiazepines Containing the 8- Hydroxyquinolinic Fragment

Marrugo-Gonzalez¹,

Orlov²,

Fernandez‐Maestre³

2016

PTQ

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“…Interactions of thiazole derivative 7 with hydroxyl amine hydrochloride in boiling ethanol in the presence of NaOH and/or in boiling pyridine yield the corresponding oxime 12 and pyrazolothiazole 14 as a second bicyclic fused heterocycle. Acetylation of oxime 12 via acetic anhydride yielded the acetoxy derivative 13 [21][22][23].…”

Section: Chemistrymentioning

confidence: 99%

Facile synthesis of new fused and non-fused heterocyclic systems from a γ-ketoacid

et al. 2014

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“…However this mechanism appears less probable since the common amine reactions with chalcones proceed at the β-С atom to form Michael adducts [16]; rare examples of 1,2-addition have been observed in chalcones reactions with p-phenylenediamine in acid or strongly alkaline environment [17,18].…”

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confidence: 99%

Reactions of polyfluorochalcones with o- and p-phenylenediamines. Synthesis and intramolecular transformations of polyfluorinated 2,4-diaryl-2,3-dihydrobenzo-1H-1,5-diazepines

Borodina

Орлова

2015

Russ J Org Chem

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Polyfluorochalcones react with o-phenylenediamine in ethanol and 2-propanol in the presence of triethylamine or benzyltriethylammonium chloride (TEBAC) affording polyfluorinated 2,4-diaryl-2,3-dihydrobenzo-1Н-1,5-diazepines. Along with the latter in the presence of triethylamine Michael aza-adducts presumably formed, and at the use of TEBAC in 2-propanol products of intramolecular cyclization and rearrangement of benzo-1,5-diazepines, dihydrobenzimidazo[1,2-a]quinolines were obtained. The reactions of polyfluorochalcones with p-phenylenediamine in ethanol or DMF proceed mostly with the substitution of the para-fluorine atom in the perfluorophenyl rings.Chalcones reaction with o-phenylenediamine is one of the main procedures of the preparation of benzo-1Н-1,5-diazepines [1], an important heterocycle class with versatile biological actions used as antidepressants, tranquilizing, antiphlogistic, anticonvulsant, antifeedant, antibacterial, and analgesic agents [2][3][4][5]. The synthesis of benzo-1,5-diazepines from chalcones and o-phenylenediamine is commonly carried out in the presence of bases, acids, or salts [1, 6-8]. It is expectable that fluorine atoms and polyfluorinated residues in the benzodiazepine molecule would significantly affect its biological properties [9, 10].We formerly investigated reactions of polyfluorinated chalcones with nitrogen binucleophiles: hydrazine hydrate, phenylhydrazine [11], o-aminothiophenol [12] leading to the formation of various polyfluorinated azaheterocycles. The preliminary communication [13] contains the description of the first results of reactions between polyfluorochalcones 1а-1с and o-phenylenediamine. In this study the number of substrates and reagents was extended and the optimization of the reaction conditions was attempted.The reaction with o-phenylenediamine was performed for polyfluorinated chalcones 1a-1i, with pphenylenediamine, for compounds 1а-1c.Taking into consideration the easy substitution of fluorine in the perfluorophenyl rings of chalcones at

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New aspects of the chemistry of 2,3-dihydro-1H-1,5-benzodiazepine

Cited by 9 publications

References 2 publications

Synthesis of 2,3-Dihydro-1h-1,5-Benzodiazepines Containing the 8- Hydroxyquinolinic Fragment

Synthesis of 2,3-Dihydro-1h-1,5-Benzodiazepines Containing the 8- Hydroxyquinolinic Fragment

Facile synthesis of new fused and non-fused heterocyclic systems from a γ-ketoacid

Reactions of polyfluorochalcones with o- and p-phenylenediamines. Synthesis and intramolecular transformations of polyfluorinated 2,4-diaryl-2,3-dihydrobenzo-1H-1,5-diazepines

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