A straightforward synthesis of novel 4<i>H</i>‐thiazolo[3,2‐<i>d</i>][1,5]benzodiazepine derivatives

Janciene, Regina; Vektarienė, Aušra; Stumbreviciute, Zita; Kosychova, Lidija; Klimavicius, Algirdas; Puodziunaite, Benedikta D.

doi:10.1002/hc.20026

Cited by 13 publications

(15 citation statements)

References 11 publications

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“…In each case the optimum reaction time was determined by tlc monitoring. Then the reaction mixture was allowed to stand overnight in a Tables 1, 2 Compounds 2g and 2h have been prepared from thiolactams 1d and 1h (5.0 mmoles) by treatment with -bromoacetaldehyde diethyl acetal (4 ml, 25.7 mmoles) in 60 ml of refluxing butan-2-one and water (0.5 ml) mixture following the method previously described by us [6] (Tables 1, 2, 3). …”

Section: Methodsmentioning

confidence: 99%

“…This was evidenced by tlc analysis which indicated slow consumption of starting material. Synthesis of the starting materials 1a-c and 1e-g have been reported in [6]. Thiolactams 1d and 1h were obtained from N 5 -unsubstituted (R 2 = H) corresponding 3-R-4-R 1 -2,3,4,5-tetrahydro-1,5-benzodiazepine-2(1H)-thiones (10, R = Me, R 1 = H; 11, R = H, R 1 = Me) [7] by acetylation or formylation.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of novel 1‐substituted [1,3]thiazolo[3,2‐a]‐[1,5]benzodiazepine derivatives from 1,5‐benzodiazepine‐2‐thiones and α‐halogen carbonyl compounds

Janciene

Stumbreviciute

Podeniene

et al. 2006

Journal of Heterocyclic Chem

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A number of substituted 4H,5H,6H‐thiazolo[3,2‐a][1,5]benzodiazepinium salts 2a‐h, 5, 9, which are based on the novel thiazolobenzodiazepine system, were prepared by condensation‐cyclization of 1,5‐benzodiazepine‐2‐thiones 1a‐f, h, 4 with α‐haloketones, as well as with α‐bromoacetaldehyde diethyl acetal. The structure and stereochemistry of the ring system obtained were investigated by 1H and 13C nmr spectroscopy: the additional heterocyclic nucleus was found to appreciably influence the conformational mobility of the heptatomic ring. Upon treatment of salt 2d with alkali the presence of the base enamine structure in solution has been postulated.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of novel 1‐substituted [1,3]thiazolo[3,2‐a]‐[1,5]benzodiazepine derivatives from 1,5‐benzodiazepine‐2‐thiones and α‐halogen carbonyl compounds

Janciene

Stumbreviciute

Podeniene

et al. 2006

Journal of Heterocyclic Chem

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“…The optimized geometries and calculated electron density parameters of benzodiazepines, benzothiophene, benzofuran were estimated in order to determine their reactivity in electrophilic substitution and Diels-Alder reactions. [10][11][12] Based on structural uniformity the relative aromaticity of the systems was predicted. The experimental stability of heterocycles was accurately described using the theoretical results.…”

Section: Methodsmentioning

confidence: 99%

A theoretical approach to the nucleophilic behavior of benzofused thieno[3,2-b]furans using DFT and HF based reactivity descriptors

Vektarienė¹,

Vektaris²,

Svoboda³

2009

Arkivoc

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131

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Calculations of traditional HF and DFT based reactivity descriptors are reported for the isomeric benzofused thieno [3,2-b]furans in order to get insight into the factors determining the nature of their interactions with electrophiles. Global reactivity descriptors such as ionization energy, molecular hardness, electrophilicity, frontier molecular orbital energies and shapes, the condensed Fukui functions, total energies were determined and used to identify the differences in the stability and reactivity of benzofused thieno[3,2-b]furans. Additionally the bond order uniformity analysis, local ionization energy and electrostatic potential energy surfaces revealed structural differences of isomeric thieno[3,2-b]furans. Calculated values lead to the conclusion that heterocyclic system in thieno [3,2-b]benzofuran is more aromatic and stable than in isomeric benzothieno [3,2-b]furan. Theoretical results are in complete agreement with the experimental results and show exceptional reactivity of C(2) atom for both isomers.

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“…Some heterocycles containing benzodiazepine moieties were also found to have anti-inflammatory, antiviral, anti-HIV-1, antimicrobial, and antitumour activities [13]. Apart from their biological importance, benzodiazepines are valuable synthons for the preparation of fused ring compounds, such as triazolo, thiazolo, imidazo and pyrimidobenzo-diazepines [14]. Although many methods for synthesizing benzodiazepine ring systems have been reported, they continue to receive much attention [11].…”

Section: Introductionmentioning

confidence: 99%

The Chemical and Structural Properties of 2-Aminobenzylamine Derivatives

El‐Shaieb¹,

Jones²

2013

Zeitschrift Für Naturforschung B

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We report a conventional and simple method to synthesize quinazoline and benzodiazepine derivatives by treatment of 2-aminobenzylamine (1) with several π-electron-deficient compounds. Quinazoline derivatives were obtained by treatment of 1 with either tetracyanoethylene or 7,7,8,8-tetracyanoquinodimethane. Benzodiazepine derivatives were formed when 1 was reacted with either 2,3-dichloro-1,4-naphthoquinone or 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Fused quinazoline and benzoazepine derivatives were formed by dry heating of 1 with either naphthalic anhydride, cis-1,2,3,6-tetrahydrophthalic anhydride, tetrachlorophthalic anhydride and/or diphenic anhydride, respectively. The NMR spectra and the mass spectrometric data as well as elemental analyses of all new products are consistent with the proposed structures. The structures of the quinazoline derivatives 26 and 28 were further confirmed by single-crystal X-ray structure determination. Plausible mechanisms for the formation of several products are discussed.

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A straightforward synthesis of novel 4H‐thiazolo[3,2‐d][1,5]benzodiazepine derivatives

Abstract: ABSTRACT:The novel 4H-thiazolo[3,2-d]

Cited by 13 publications

References 11 publications

Synthesis of novel 1‐substituted [1,3]thiazolo[3,2‐a]‐[1,5]benzodiazepine derivatives from 1,5‐benzodiazepine‐2‐thiones and α‐halogen carbonyl compounds

Synthesis of novel 1‐substituted [1,3]thiazolo[3,2‐a]‐[1,5]benzodiazepine derivatives from 1,5‐benzodiazepine‐2‐thiones and α‐halogen carbonyl compounds

A theoretical approach to the nucleophilic behavior of benzofused thieno[3,2-b]furans using DFT and HF based reactivity descriptors

The Chemical and Structural Properties of 2-Aminobenzylamine Derivatives

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