Regioselective Synthesis of Novel 4,4′-and 5,5′-bi-(1,2,4-triazole) Derivatives

Farag, Ahmad M.; Dawood, Kamal M.; Khedr, Nabila A.

doi:10.3184/030823407x237876

Cited by 14 publications

(3 citation statements)

References 17 publications

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“…Elemental analyses were carried out at the Microanalytical center of Cairo University. 2-cyano-3phenyl-2-pentenedinitrile (2) [15], heterocyclic diazonium salts 3a-e [25][26][27][28], hydrazonyl halides 12a-c [29,30] and 1-(benzothiazol-2-yl)-2-bromoethanone 15 [31] were prepared following the reported literature procedures.…”

Section: Methodsmentioning

confidence: 99%

ChemInform Abstract: Fused Polyaza‐heterocycles and 1,3,4‐Thiadiazoles via a Tricyano Synthon.

Dawood

Raslan

2008

ChemInform

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Section: Methodsmentioning

confidence: 99%

ChemInform Abstract: Fused Polyaza‐heterocycles and 1,3,4‐Thiadiazoles via a Tricyano Synthon.

Dawood

Raslan

2008

ChemInform

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“…There are in the literature a few examples where compounds with exocyclic C=N bonds were used as dipolarophiles. However, the available data demonstrated a good reactivity of the imino group in comparison with the trisubstituted bond in alkenes [ 16 ]. In all cases, the addition of nitrile imines to the C=N bond occurs regioselectively with the formation of 1,2,4-triazole [ 1 ].…”

Section: Introductionmentioning

confidence: 99%

[3+2]-Cycloaddition of Nitrile Imines to Parabanic Acid Derivatives—An Approach to Novel Spiroimidazolidinediones

Kuznetsova,

Tkachenko,

Petrovskaya

et al. 2023

IJMS

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Approximately 1,3-Dipolar cycloaddition of imidazolidine derivatives containing exocyclic double bonds is a convenient method of creating spiro-conjugated molecules with promising anticancer activity. In this work, the derivatives of parabanic acid (2-thioxoimidazolidine-4,5-diones and 5-aryliminoimidazolidine-2,4-diones) were first investigated as dipolarophiles in the reactions with nitrile imines. The generation of nitrile imines was carried out either by the addition of tertiary amine to hydrazonoyl chlorides «drop by drop» or using the recently proposed diffusion mixing technique, which led to ~5–15% increases in target compound yields. It was found that the addition of nitrile imines to C=S or C=N exocyclic double bonds led to 1,2,4-thiazolines or triazolines and occurred regioselectively in accordance with the ratio of FMO coefficients of reactants. The yield of the resulting spiro-compound depended on the presence of alkyl substituents in the nitrile imine structure and was significantly decreased in reactions with imines with strong electron donor or electron-withdrawing groups. Some of the obtained compounds showed reasonable in vitro cytotoxicity. IC50 values were calculated for HCT116 (colon cancer) cells using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) test.

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“…There are in the literature a few examples where compounds with an exocyclic C=N bonds were used as dipolarophiles. However, the available data demonstrated a good reactivity of the imino group in comparison with the trisubstituted bond in alkenes [14]. In all cases, the addition of nitrile imines to the C=N bond occurs regioselectively with the formation of 1,2,4-triazole [1].…”

Section: Introductionmentioning

confidence: 99%

[3+2]-Cycloaddition of Nitrile Imines to Parabanic Acid Derivatives – an Approach to Novel Spiroimidazolidinediones

Kuznetsova,

Tkachenko,

Petrovskaya

et al. 2023

Preprint

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1,3 Dipolar cycloaddition of imidazolidine derivatives containing exocyclic double bonds is a convenient method of creating spiro-conjugated molecules with the promising anticancer active. In this work, the derivatives of parabanic acid (2-thioxoimidazolidine-4,5-diones and 5-aryliminoimidazolidine-2,4-diones) were firstly investigated as dipolarophiles in the reactions with nitrile imines. The generation of nitrile imines was carried out either by the addition of tertiary amine to hydrazonoyl chlorides «drop by drop» or using recently proposed diffusion mixing technique, which led to ~5-15% increasing of target compounds yields. It was found that the addition of nitrile imines to C=S or C=N exocyclic double bonds led to 1,2,4-thiazolines or triazolines and occurred regioselectively in accordance to the ratio of FMO coefficients of reactants. The yield of the resulting spiro-compound depended on the presence of alkyl substituents in nitrile imine structure and was significantly decreases at the reactions with imines with strong electron donor or electron-withdrawing groups. Some of the obtained compounds showed reasonable in vitro cytotoxicity. IC50 values were calculated for HCT116 (colon cancer) cells using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) test.

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Regioselective Synthesis of Novel 4,4′-and 5,5′-bi-(1,2,4-triazole) Derivatives

Abstract: A regioselective synthesis is reported of a series of polysubstituted 1,2,4-triazoles and 4,4′- and 5,5′-bi-(1,2,4-triazoles) via 1,3-dipolar cycloaddition reactions of nitrilimines with some aza- and diaza-butadiene derivatives.

Cited by 14 publications

References 17 publications

ChemInform Abstract: Fused Polyaza‐heterocycles and 1,3,4‐Thiadiazoles via a Tricyano Synthon.

ChemInform Abstract: Fused Polyaza‐heterocycles and 1,3,4‐Thiadiazoles via a Tricyano Synthon.

[3+2]-Cycloaddition of Nitrile Imines to Parabanic Acid Derivatives—An Approach to Novel Spiroimidazolidinediones

[3+2]-Cycloaddition of Nitrile Imines to Parabanic Acid Derivatives – an Approach to Novel Spiroimidazolidinediones

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