Microwave‐Induced Conversion of Acid Hydrazides to N,N′‐Diacylhydrazines in Solvent‐Free Conditions

Sailu, B.; Komaraiah, A.; Reddy, P. S. N.

doi:10.1080/00397910600602677

Cited by 6 publications

(5 citation statements)

References 8 publications

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“…It has been reported that chlorine may be a weak proton acceptor. 4,11 For the sake of comparison, compound 9, 12 an analogue to 1, was also prepared. Compounds 1-4 and 8 are soluble in solvents of low polarity, such as chloroform and dichloromethane, whereas dichloride 9 is soluble only in polar solvents such as methanol and dimethyl sulfoxide.…”

Section: Resultsmentioning

confidence: 99%

“…The structures of compounds 5 − 7 have been briefly described in reported works. 10a,c,h The synthetic routes for compounds 1 − 4 , 8 , and 9 are presented in 1. It has been reported that chlorine may be a weak proton acceptor. , For the sake of comparison, compound 9 , an analogue to 1 , was also prepared. Compounds 1 − 4 and 8 are soluble in solvents of low polarity, such as chloroform and dichloromethane, whereas dichloride 9 is soluble only in polar solvents such as methanol and dimethyl sulfoxide.…”

Section: Resultsmentioning

confidence: 99%

“…Compound 9. Compound 21 (0.28 g, 1.78 mmol) and HATU (0.74 g, 2.00 mmol) were dissolved in DMF (10 mL). To the solution was added a solution of 22 (0.30 g, 1.78 mmol) and diisopropylethylamin (DIEA) (3 mL) in DMF (10 mL).…”

Section: Methodsmentioning

confidence: 99%

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F···H−N and MeO···H−N Hydrogen-Bonding in the Solid States of Aromatic Amides and Hydrazides: A Comparison Study

朱元元

邬静

Chuang

et al. 2007

Crystal Growth & Design

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Four intramolecularly F···H−N hydrogen-bonded aromatic amide and hydrazide derivatives have been prepared. Their crystal structures are investigated and compared with those of their MeO···H−N hydrogen-bonded analogues. It is found that all the F···H−N hydrogen-bonded molecules form intermolecular CO···H−N hydrogen bonding and, for two of them, weak F···H−C interactions. In contrast, the MeO···H−N hydrogen-bonded molecules display only very weak intermolecular C−H···π interactions. The hydrogen-bonded amide units in the fluorine-bearing molecules exhibit large torsion from the connecting benzene units. This has been attributed to the weaker ability of fluorine as a hydrogen-bonding acceptor, its smaller size (relative to the MeO group), and consequently the strengthened intermolecular NH···OC hydrogen bonding. The results also suggest that, although the weakness of fluorine as a hydrogen-bonding acceptor has been mainly attributed to its low polarizability and tightly contracted lone pairs, the great tendency of fluorine-bearing aromatic amides to form intermolecular CO···H−N hydrogen bonding may also play a role.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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F···H−N and MeO···H−N Hydrogen-Bonding in the Solid States of Aromatic Amides and Hydrazides: A Comparison Study

朱元元

邬静

Chuang

et al. 2007

Crystal Growth & Design

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“…[19] This is possibly because of more electrophilic character of the carbonyl carbon in aliphatic hydrazides rather than aromatic ones, such that the lone pair of N attacks the carbonyl carbon in aliphatic unit readily and gives the corresponding homo-coupled product after elimination of a hydrazine unit. [23] A methodology is useful in practical sense when it can be reproduced in an industrial scale. Hence, we have explored the applicability of this methodology in large (gram) scale.…”

Section: Resultsmentioning

confidence: 99%

“…However, the aliphatic chains like the hydrazides obtained from capric acid ( 3 t ), myristic acid ( 3 u ) and palmitic acid ( 3 v ) reacted in a different way giving the corresponding homocoupled amide derivatives in all the cases ( 4 t – v ) (Table 3). [19] This is possibly because of more electrophilic character of the carbonyl carbon in aliphatic hydrazides rather than aromatic ones, such that the lone pair of N attacks the carbonyl carbon in aliphatic unit readily and gives the corresponding homo‐coupled product after elimination of a hydrazine unit [23] …”

Section: Resultsmentioning

confidence: 99%

Co(II) Acetate‐Assisted Direct Synthesis of Acyl Hydrazones from Acyl Hydrazides under Mild Conditions

Pal,

Das,

et al. 2023

Chemistry An Asian Journal

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Acyl hydrazones are a class of synthetically important organic compounds that are recurrently in high demand for synthesis and use in various fields of chemistry and biology. We report the first Co(II) catalyzed one‐component one‐pot sustainable synthesis of acyl hydrazones only from acyl hydrazides under mild reaction conditions. Traditional and contemporary methodologies use two components (usually acyl hydrazides and aldehydes/ketones/alcohols/styrene) as the coupling partners. Our protocol, on the other hand, involves the in situ generation of aldehyde intermediate (detected by gas chromatography) from the acyl hydrazide, which then undergoes condensation with another molecule of the same acyl hydrazide in the same pot to yield acyl hydrazones in presence of mild base K2CO3 and low‐cost Co(OAc)2 ⋅ 4H2O as catalyst. This method shows good functional group tolerance with good to excellent yield of products. Furthermore, some of the resulting acyl hydrazones have been used as synthetic precursors and explored in various post‐synthetic modifications to afford N‐heterocyclic compounds. Furthermore, photoswitchable properties of few synthesized acyl hydrazones are also explored using their E/Z isomerization around the C=N bond, as realized by high‐pressure liquid chromatography (HPLC) and UV‐vis spectroscopic studies.

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