Synthesis of Substituted 5,6-Dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepines

Kosychova, Lidija; Stumbreviciute, Zita; Pleckaitiene, L.; Janciene, Regina; Puodziunaite, Benedikta D.

doi:10.1023/b:cohc.0000040781.41929.9c

Cited by 12 publications

(11 citation statements)

References 10 publications

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“…After completion of reaction (monitored by TLC), the precipitate was collected by filtration, washed and recrystallised from EtOH-DMF to afford products 3a-h as green-blue powders in 35-44% yield. 11-[(4-Chlorophenyl)amino]- 6,9,10,e]- [1,4] …”

Section: Reactions Of 2-amino-n′-arylbenzamidines (1a-d) With 23-dicmentioning

confidence: 99%

Synthesis of Dibenzo[b,e][1,4]Diazepine Derivatives

El‐Shaieb

Hassan

Abdel-Aal

2011

Journal of Chemical Research

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The reaction of (Z)-2-amino-N'-arylbenzamidines with both 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 2,3,5,6tetrachloro-1,4-benzoquinone have been studied. The reactions were carried at room temperature overnight in dry ethyl acetate and proceed via a charge transfer complexe to give dibenzo[b,e][1,4]diazepine derivatives in 35-44% yield. Benzodiazepine derivatives have anti-inflammatory, antiviral, antimicrobial, antileukaemic, antiplatelet, anticonvulsant, antianxiety, antidepressive and antitumour activities. The products were fully characterised according to their spectral analyses.

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Section: Reactions Of 2-amino-n′-arylbenzamidines (1a-d) With 23-dicmentioning

confidence: 99%

Synthesis of Dibenzo[b,e][1,4]Diazepine Derivatives

El‐Shaieb

Hassan

Abdel-Aal

2011

Journal of Chemical Research

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“…5 Thus, considerable attention has been directed towards the synthesis of polycyclic 1,4-benzodiazepines, as well as the 1,5-isomers. 6 Recently, many novel compounds containing heterocyclic ring systems such as triazole, thiazole, imidazole, quinoline, oxadiazole, pyran, oxazole, furan and pyrimidine annelated to the bicyclic 1,5-benzodiazepine have been synthesized by our [7][8][9][10][11][12] and other research groups. 6,13,14 Fused quinazolinones are important heterocyclic compounds with widespread occurrence in alkaloids possessing diverse biological activity.…”

Section: Introductionmentioning

confidence: 99%

Novel synthesis of quinazolino[3,2-a][1,5]benzodiazepines: an experimental and computational study

Janciene¹,

Javorskis²,

Mikulskiene³

et al. 2015

Arkivoc

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[ [1,5]benzodiazepin-13(5H)-one derivatives were synthesized in a one-step sequential acylation-cyclization reaction with a simple procedure from an appropriate 5-substituted 3-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one and 2-sulfinylaminobenzoyl chlorides. The mechanism of the heterocyclization reaction was studied by the DFT method using the B3LYP functional and 6-31+G(d, p) basis set.

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“…1 It is known, in fact, that the pharmaceutical activity appears to be exchanged when different heterocyclic rings are annelated to the basic 1,4-and 1,5-benzodiazepine systems. 1,2 In previous papers we have reported the synthesis of polycyclic peri-annelated imidazo [1,5]benzodiazepines 3 and derivatives containing imidazo 4 , triazolo 5 and thiazolo 6 nucleus fused to the "a" edge of the seven-membered ring of the 1,5-benzodiazepine system. In continuation of our investigation on tricyclic benzodiazepines, we have extended the cycloaddition strategy to develop a synthetic pathway towards 1,5-benzodiazepines including a 1,2,4-oxadiazole nucleus.…”

Section: Introductionmentioning

confidence: 99%

“…7 A cyclofunctionalization strategy is based on exploiting the reactivity of the C=S group of the corresponding derivatives towards some nucleophiles, such as hydroxylamine. In recent years, some [1,2,4]oxadiazolo [1,5]benzodiazepine derivatives were prepared via the 1,3-dipolar cycloaddition to the dipolarophile C=N moiety of the diazepine skeleton.…”

Section: Introductionmentioning

confidence: 99%