A convenient synthesis of novel [1,2,4]oxadiazolo[4,3-a][1,5]benzodiazepine derivatives

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

doi:10.3998/ark.5550190.0012.b08

Cited by 5 publications

(4 citation statements)

References 8 publications

(14 reference statements)

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“…Yellow solid is washed with big amount of cold chloroform and dried. -2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl) 10.72 (1H, s, 5 -NH). 13 Benzoyl-3-methyl-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl) 10.71 (1H, s, 5 -NH).…”

Section: Methodsmentioning

confidence: 99%

“…-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl) 10.72 (1H, s, 5 -NH). 13 Benzoyl-3-methyl-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl) 10.71 (1H, s, 5 -NH). 13 and the reaction mixture was stirred at room temperature for 2-3 h. After completion of reduction, as observed by TLC monitoring, the reaction mixture was filtered.…”

Section: Methodsmentioning

confidence: 99%

“…In a quest to find additional potential quinazoline-based derivatives, various substituted quinazolinones 2,3 and compounds encompassing a quinazolino [1,4]benzodiazepine moiety in their skeleton [4][5][6][7] have been developed. As a part of our ongoing research activity, [8][9][10] we were interested in the synthesis of some quinazolino [1,5]benzdiazepine derivatives as possible analogues of natural products. The main synthetic routes to compounds with quinazolino [1,4]benzodiazepine moiety utilize the implementations of 2-azidobenzoylamides in aza-Wittig methodology 4,5,11 and transition metal-…”

Section: Introductionmentioning

confidence: 99%

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A combined experimental and theoretical study of the synthesis of quinazolino[3,2-a][1,5]benzodiazepin-13-ones

Janciene¹,

Vektarienė²,

Mikulskiene³

et al. 2013

Arkivoc

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A simple and efficient general approach to various tetracyclic 6,7-dihydroquinazolino[3,2-a] [1,5]benzodiazepin-13(5H)-ones has been demonstrated by reductive N-heterocyclization of 5-alkyl-or benzoyl-1-(2-nitrobenzoyl)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-ones. These 2-nitrobenzoylamides were obtained by acylation of the starting 5-alkyl-or benzoyl-1,5-benzodiazepin-2-ones with 2-nitrobenzoyl chloride. A theoretical understanding of the features of the reductive N-heterocyclization reaction was provided by means of quantum chemical reactivity descriptors calculations.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A combined experimental and theoretical study of the synthesis of quinazolino[3,2-a][1,5]benzodiazepin-13-ones

Janciene¹,

Vektarienė²,

Mikulskiene³

et al. 2013

Arkivoc

Self Cite

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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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Dihydroquinazolino[3,2‐a][1,5]benzodiazepines: Synthesis and Computational Study of Reductive N‐Heterocyclization of N‐(2‐Nitrobenzoyl)‐1,5‐benzodiazepin‐2‐ones

Janciene

Mikulskiene

Javorskis

et al. 2014

Journal of Heterocyclic Chem

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A number of 6,7‐dihydroquinazolino[3,2‐a][1,5]benzodiazepin‐13(5H)‐ones were prepared utilizing the coupling of readily available 5‐acyl‐1,3,4,5‐tetrahydro‐2H‐1,5‐benzodiazepin‐2‐ones with 2‐nitrobenzoyl chloride followed by a reductive N‐heterocyclization. 3‐Methylsubstituted 1‐(2‐nitrobenzoyl)‐1,5‐benzodiazepinone derivatives did not cyclize under the reductive N‐heterocyclization conditions. The possible mechanism of this heterocyclization was discussed, and it was demonstrated that the hydroxylamine intermediate was the initiator of this reaction. To clarify the reasons of different reactivities of various 1,5‐benzodiazepine derivatives, the quantum‐chemical reactivity descriptors of the hydroxylamine intermediates were calculated and evaluated.

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A convenient synthesis of novel [1,2,4]oxadiazolo[4,3-a][1,5]benzodiazepine derivatives

Cited by 5 publications

References 8 publications

A combined experimental and theoretical study of the synthesis of quinazolino[3,2-a][1,5]benzodiazepin-13-ones

A combined experimental and theoretical study of the synthesis of quinazolino[3,2-a][1,5]benzodiazepin-13-ones

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

Dihydroquinazolino[3,2‐a][1,5]benzodiazepines: Synthesis and Computational Study of Reductive N‐Heterocyclization of N‐(2‐Nitrobenzoyl)‐1,5‐benzodiazepin‐2‐ones

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