Synthesis of [1,2‐a] benzimidazolo‐1,3,5‐triazin‐2‐thione, [1,2‐a] benzimidazolo‐1,3,5‐thiadiazin‐2‐thione, [1,2‐a] benzimidazolo‐1,3,5‐triazin‐2‐amine, and [1,2‐a] benzimidazol‐2‐yl amidrazone

Hajri, Azhar; Abderrahim, Raoudha

doi:10.1002/hc.20618

Cited by 6 publications

(2 citation statements)

References 13 publications

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“…A reaction of N ‐benzimidazol‐2‐yl iminoester with carbon disulfide in the presence of triethylamine and under reflux in ethanol also afforded 1,3,5‐triazino [1,2‐a]benzimidazolo‐2‐thione (Scheme b) . Herein, we present a novel method for the synthesis of tetraazatricyclic compounds.…”

Section: Introductionmentioning

confidence: 98%

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A New Synthetic Method for Tetraazatricyclic Derivatives and Evaluation of Their Biological Properties

et al. 2018

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A new method for the synthesis of tetraazatricyclic compounds by a reaction of benzoyl isothiocyanates with 2‐aminobenzimidazole is presented and a possible mechanism proposed. The new base‐catalyzed degradation of the tetraazatricyclic ring has been carried out. A reaction of benzoyl isothiocyanate with 2‐aminobenzoxazole, however, resulted in the formation of 3‐benzoyl‐1‐(2‐hydroxyphenyl)urea while a reaction with 2‐aminobenzothiazole gave 3‐(1,3‐benzothiazol‐2‐yl)‐1‐(benzoyl)thiourea. Density functional theory computed reaction mechanism for the formation of tetraazaatricyclic compounds is discussed. Biological screening of the compounds against Plasmodium falciparium and HIV‐1 protease showed very little activity but they were moderately active against Trypanosoma brucei with an IC50 of 19.71 μM for 11‐(3‐methoxyphenyl)‐1,8,0,12‐tetraazatricyclo [7.4.0.02,7]trideca‐2(7),3,5,9,11‐pentaene‐13‐thione (4).

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Section: Introductionmentioning

confidence: 98%

“…Tetraazatricyclics with aliphatic side chains have been synthesized before by different methods. N ‐benzimidazol‐2‐yl iminoester has been heated with thiourea in dry toluene under reflux for 48 h to afford 1,3,5‐triazino [1,2‐a]benzimidazolo‐2‐thione (Scheme a) …”

Section: Introductionmentioning

confidence: 99%

A New Synthetic Method for Tetraazatricyclic Derivatives and Evaluation of Their Biological Properties

et al. 2018

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ChemInform Abstract: Synthesis of [1,2‐a] Benzimidazolo‐1,3,5‐triazin‐2‐thione, [1,2‐a] Benzimidazolo‐1,3,5‐thiadiazin‐2‐thione, [1,2‐a] Benzimidazolo‐1,3,5‐triazin‐2‐amine, and [1,2‐a] Benzimidazolo‐2‐yl Amidrazone.

Hajri¹,

Abderrahim²

2010

ChemInform

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Synthesis of [1,2-a] Benzimidazolo-1,3,5-triazin-2-thione, [1,2-a]Benzimidazolo-1,3,5-thiadiazin-2-thione, [1,2-a] Benzimidazolo-1,3,5-triazin-2-amine, and [1,2-a] Benzimidazolo-2-yl Amidrazone. -In view of the potential biological activity of benzimidazoles and their polycyclic derivatives, the fused benzimidazoles (III), (VII), and (IX) as well as the benzimidazolyl amidrazones (V) are synthesized using operationally simple methods. The intramolecular cyclization of (V) seems to be possible, but its cyclization fails, which is rationalized by the lower nucleophilicity of the NH-nitrogen atom. -(HAJRI, A.; ABDERRAHIM*, R.; Heteroat. Chem. 21 (2010) 5, 279-283,

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Bicyclic 5-6 Systems With One Bridgehead (Ring Junction) Nitrogen Atom: Three Extra Heteroatoms 1:2

David¹

2022

Comprehensive Heterocyclic Chemistry IV

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Synthesis of [1,2‐a] benzimidazolo‐1,3,5‐triazin‐2‐thione, [1,2‐a] benzimidazolo‐1,3,5‐thiadiazin‐2‐thione, [1,2‐a] benzimidazolo‐1,3,5‐triazin‐2‐amine, and [1,2‐a] benzimidazol‐2‐yl amidrazone

Abstract: N-benzimidazol-2-yl imidate type 1 reacts with thiourea, carbon disulfide, cyanamide, and hydrazide to

Cited by 6 publications

References 13 publications

A New Synthetic Method for Tetraazatricyclic Derivatives and Evaluation of Their Biological Properties

A New Synthetic Method for Tetraazatricyclic Derivatives and Evaluation of Their Biological Properties

ChemInform Abstract: Synthesis of [1,2‐a] Benzimidazolo‐1,3,5‐triazin‐2‐thione, [1,2‐a] Benzimidazolo‐1,3,5‐thiadiazin‐2‐thione, [1,2‐a] Benzimidazolo‐1,3,5‐triazin‐2‐amine, and [1,2‐a] Benzimidazolo‐2‐yl Amidrazone.

Bicyclic 5-6 Systems With One Bridgehead (Ring Junction) Nitrogen Atom: Three Extra Heteroatoms 1:2

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