ChemInform Abstract: OXIDATION OF HYDRAZIDES OF SALICYLIC AND SUBSTITUTED SALICYLIC ACIDS WITH ACTIVE MANGANESE DIOXIDE

Haksar, C. N.; Malhotra, Rashmi; Ramachandran, P. K.

doi:10.1002/chin.197950120

Cited by 2 publications

(3 citation statements)

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“…The slow reaction rate of desoxy-CDX versus the inactivity of QX indicates that the side chain of CDX and desoxy-CDX can also react with MnO 2 but with a much lower reactivity than the N -oxide moiety. This observation is consistent with the susceptibility of hydrazide (−CO−NH−N<) or hydrazone (> CHNN<) moieties toward oxidation reactions ( , ).…”

Section: Resultssupporting

confidence: 87%

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Reactivity and Transformation of Antibacterial N-Oxides in the Presence of Manganese Oxide

Zhang

Huang

2004

Environ. Sci. Technol.

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Organic N-oxides are an important structural class in many pharmaceutical and industrial chemicals. Little is known aboutthe potential transformation of organic N-oxides at the sediment-water interface. Veterinary antibacterial agents carbadox and olaquindox are examples of commonly used heterocyclic N-oxides. Investigation with various N-oxides including carbadox, olaquindox, quinoline N-oxide, and quindoxin revealed surprisingly high reactivity toward MnO2 for all of the compounds except olaquindox. Desoxycarbadox and quinoxaline, two structurally related compounds that lack an N-oxide functional group, showed much lower or no reactivity toward MnO2. Comparisons among the previous compounds indicate that N-oxide moiety is the primary reactive site to MnO2, and substitution at the alpha-C adjacent to the N-oxide group is critical in determining the overall reactivity. Reactions of N-oxides with MnO2 appeared to be oxidation, with generation of Mn2+ parallel to degradation of the parent organics. Product characterization confirmed that quinoline N-oxide and quindoxin transformed into 2-hydroxyquinoline and quinoxaline 2,3-diol, respectively, in reactions with MnO2. The transformation involves separate steps of N-oxide moiety deoxygenation and neighboring alpha-C hydroxylation as elucidated by 18O isotope experiments. All of the experimental results pointed to a mechanism that involves an N-oxide radical intermediate. This is the first study to report such transformation reactivity of organic N-oxides toward manganese oxide, offering a new degradation pathway that could be important for the fate of this group of compounds in the aquatic environment.

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Section: Resultssupporting

confidence: 87%

“…Hydrazines (-NH-NH-) and hydrazides (-CO-NH-NH-) have been oxidized to azo compounds (sNdNs) by several oxidizing agents, including MnO 2 (22,23,40), silver (I) oxide (35), cobalt salts (41), phenylseleninic acid (42), and enzymes (43). The formed azo compounds would lose N2 to generate radicals.…”

Section: Introductionmentioning

confidence: 99%

Reactivity and Transformation of Antibacterial N-Oxides in the Presence of Manganese Oxide

Zhang

Huang

2004

Environ. Sci. Technol.

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“…All the intermediate‐substituted acylhydrazines were synthesized according references, and the m.p. of these intermediates accorded with references (27–37).…”

Section: Methodssupporting

confidence: 66%

Synthesis of Some N, N′‐Diacylhydrazine Derivatives with Radical‐Scavenging and Antifungal Activity

Liu¹,

Shi²,

Ma³

et al. 2009

Chem Biol Drug Des

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These authors contributed equally to this work.A series of N,N¢-diacylhydrazines were prepared and their structures were confirmed by 1 H NMR, MS and FTICR-MS. They were tested radical-scavenging activity in vitro. The preliminary bioassays of title compounds showed that two compounds had excellent radical-scavenging activity comparable with vitamin C, while the activity is highly relative to the substituents. Surprisingly, several compounds also exhibit favorable fungicidal activities. To further explore the comprehensive structureactivity relationships about the fungicidal activity, a three-dimensional quantitative structure-activity relationship analysis using the method of comparative molecular field analysis was performed.

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ChemInform Abstract: OXIDATION OF HYDRAZIDES OF SALICYLIC AND SUBSTITUTED SALICYLIC ACIDS WITH ACTIVE MANGANESE DIOXIDE

Abstract: Die Oxidation der Hydrazide (I) mit aktivem MnO2 in verschiedenen Lösungsmitteln führt zur Bildung der entsprechenden Säuren (II).

Cited by 2 publications

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Reactivity and Transformation of Antibacterial N-Oxides in the Presence of Manganese Oxide

Reactivity and Transformation of Antibacterial N-Oxides in the Presence of Manganese Oxide

Synthesis of Some N, N′‐Diacylhydrazine Derivatives with Radical‐Scavenging and Antifungal Activity

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