Reductive fission of azoarenes to aminoarenes by aluminium/hydrazine hydrate

Päsha, M. A.; Nanjundaswamy, H. M.

doi:10.3184/0308234043431645

Cited by 10 publications

(7 citation statements)

References 24 publications

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“…In both cases the reaction was complete in just 20 minutes as confirmed by TLC analysis and provided the corresponding arylamines in 90% and 88%, respectively. 23,24 in methanol at 65°C takes about 1.8-2.5 hours for completion with satisfactory yields. But in our method, the reduction of nitroarenes to arylamines with iron powder (3.0 equiv) and calcium chloride (1.0 equiv) in a solvent mixture of ethanol and water goes to completion within 25-30 minutes at 60°C with good yields as shown in Table 2.…”

Section: Scheme 1 Reduction Of Aryl Nitro Compoundsmentioning

confidence: 99%

An Efficient Method for Aryl Nitro Reduction and Cleavage of Azo Compounds Using Iron Powder/Calcium Chloride

Chandrappa¹,

Vinaya²,

Ramakrishnappa³

et al. 2010

Synlett

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A novel, efficient Fe/CaCl 2 system is revealed for the reduction of nitroarenes and reductive cleavage of azo compounds by catalytic transfer hydrogenation (CTH). The selective reduction of nitro compounds in the presence of sensitive functional groups including halides, carbonyl, hydroxyl, aldehyde, methyl, methoxy, acetyl, nitrile, and ester substituents with an excellent yields is reported. The simple experimental procedure and easy purification make the protocol advantageous.

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Section: Scheme 1 Reduction Of Aryl Nitro Compoundsmentioning

confidence: 99%

An Efficient Method for Aryl Nitro Reduction and Cleavage of Azo Compounds Using Iron Powder/Calcium Chloride

Chandrappa¹,

Vinaya²,

Ramakrishnappa³

et al. 2010

Synlett

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“…Reductive cleavage of the azo functionality is a crucial step for unmasking two different amine synthons. Hydrazine hydrate is widely used for symmetrical reductive cleavage of the azo moiety . The access of a nitrogenous compound by the unprecedented cleavage of an azo unit is fascinating for subsequent organic transformations …”

Section: Introductionmentioning

confidence: 99%

Azouracil and Its Cu(II)-Catalyzed Cyclization to an Anticancer Active Triazole Derivative: Symmetrical and Asymmetrical Reductive Cleavage, DNA Interaction, and Molecular Docking Studies

Banerjee

Ghosh

Pradhan

et al. 2019

ACS Appl. Bio Mater.

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The 6-amino-1,3-dimethyl uracil-based azo derivative (p-carboxy phenylazouracil, L11) undergoes Cu(II)-catalyzed cyclization to a triazole derivative, namely, 1,3-dimethyl-8-(p-carboxy phenyl) azapurine (L11P). Interestingly, the azo functionality of L11 undergoes both symmetrical and asymmetrical reductive cleavage at two different reaction conditions. The chloride salts of Mn(II), Ni(II), and Pd(II) catalyze reductive cleavage of an azo moiety in an asymmetric manner, producing a new uracil hydrazine derivative (A3). On the other hand, hydrazine catalyzes symmetrical reductive cleavage of the azo moiety of L11, resulting in 5,6-diamino-1,3-dimethyl uracil (A2) along with the starting p-aminobenzoic acid (A1). Time-dependent density functional theoretical (TD-DFT) studies provide optimized geometries of L11, L11P, and A3 along with their orbital energies. The L11 and L11P bind firmly to genomic DNA of E. coli with a site size n ∼ 9 and n ∼ 8. The L11P shows anticancer activity on selected murine lymphoma cancer cell lines (DL, YAC1, and 2PK3). In addition, its antiproliferative activity is measured with several cancer cell lines and found hemocompatible toward blood cells. Corresponding molecular docking studies of L11P with caspase-3 (cysteine-aspartic proteases) unlock their mode of interaction.

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“…They show good biodegradability and low toxicity, so they are defined as environmentally friendly (11). Amides and anilides are also important in pharmaceutical, agrochemical industries, and are used as protecting groups in organic synthesis (12,13). It has been proved that some of the fatty acid amides and anilides synthesized have good activity against gram-positive bacteria (14).…”

Section: Introductionmentioning

confidence: 99%

Anticancer Activities of Even Numbered Monoketo Eicosanoic Acid Anilides and Semicarbazones

Onar

Anlaş

Yaşa

et al. 2019

Journal of the Turkish Chemical Society Section A: Chemistry

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This work was carried out on the cytotoxic activity of semicarbazone and anilide derivatives of ketoeicosanoic acids on canine mammary tumor cell line (CMT-U27). Five semicarbazone compounds (1-5) and five anilide compounds (6-10) were used in this study. 8-Semicarbazone eicosanoic acid (3) was shown to be cytotoxic. In contrast, 10-keto eicosanoic acid anilide (9) has been shown to be less cytotoxic towards CMT-U27 cell line.

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Reductive fission of azoarenes to aminoarenes by aluminium/hydrazine hydrate

Cited by 10 publications

References 24 publications

An Efficient Method for Aryl Nitro Reduction and Cleavage of Azo Compounds Using Iron Powder/Calcium Chloride

An Efficient Method for Aryl Nitro Reduction and Cleavage of Azo Compounds Using Iron Powder/Calcium Chloride

Azouracil and Its Cu(II)-Catalyzed Cyclization to an Anticancer Active Triazole Derivative: Symmetrical and Asymmetrical Reductive Cleavage, DNA Interaction, and Molecular Docking Studies

Anticancer Activities of Even Numbered Monoketo Eicosanoic Acid Anilides and Semicarbazones

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