Insertion and fragmentation of 2‐ferrocenylmethylidene‐1, 3‐diketones upon their reactions with <i>N</i>‐methylhydrazine

Klimova, Elena I.; López, Eduardo A. Vázquez; Mendoza, Juan Manuel Martínez; Ramirez, L. Ruiz; Flores-Álamo, Marcos; Backinowsky, Leon V.

doi:10.1002/jhet.94

Cited by 6 publications

(2 citation statements)

References 18 publications

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“…The starting compounds 1 , 2 , 3a , and 3b , unlike 2‐ferrocenylmethylidene‐1,3‐diketones [1], react with N ‐alkylhydrazines 5a , 5b at ambient temperature to yield ethyl 1‐alkyl‐5‐aryl(methyl)‐3‐ferrocenylpyrazole‐4‐carboxylates ( 6a , 6b , 6c , 6d , 6e ) (∼50%) and the insertion products, viz ., ethyl ( N ′‐acyl‐ N ′‐alkylhydrazino)‐3‐ferrocenylpropanoates ( 7a , 7b , 7c , 7d , 7e ) (∼20%) and 1‐acyl‐2‐( N ′‐alkyl‐ N ′‐ethoxycarbonylhydrazino)‐2‐ferrocenylethanes ( 8a , 8b , 8c , 8d , 8e ) (∼10%) (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…Recently, we have reported [1] that the reactions of 2‐ferrocenylmethylidene‐1,3‐diketones with N ‐methylhydrazine afford insertion products, viz ., 1‐( N ′‐acyl‐ N ′‐methylhydrazino)‐2‐acyl‐1‐ferrocenylethanes (∼40–58%), together with small amounts of fragmentation products with the loss of one acyl group rather than the expected ferrocenylpyrazole derivatives (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

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Cover Picture: Isolatable Organophosphorus(III)–Tellurium Heterocycles (Chem. Eur. J. 3/2014)

Nordheider

Chivers

Schön

et al. 2014

Chemistry A European J

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Phosphorus sulfides have been known for over 270 years and are familiar to us in strike‐anywhere matches, which contain P4S3. Many phosphorus–sulfur and phosphorus–selenium compounds have been discovered and characterized but, in contrast, phosphorus–tellurium compounds are quite rare, since it is difficult to stabilise the PTe and PTe bonds. In their Full paper on J. D. Woollins and co‐workers present the first crystal structures of organophosphorus(III)–tellurium heterocycles, which can be stabilized and structurally characterized by the appropriate choice of bulky substituents or the installation of a PV2N2 anchor.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Cover Picture: Isolatable Organophosphorus(III)–Tellurium Heterocycles (Chem. Eur. J. 3/2014)

Nordheider

Chivers

Schön

et al. 2014

Chemistry A European J

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ChemInform Abstract: Insertion and Fragmentation of 2‐Ferrocenylmethylidene‐1,3‐diketones upon Their Reactions with N‐Methylhydrazine.

et al. 2009

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Organo-iron compounds S 7100Insertion and Fragmentation of 2-Ferrocenylmethylidene-1,3-diketones upon Their Reactions with N-Methylhydrazine. -Diketones, e.g. (I), react with N-methylhydrazine (II) to afford mainly insertion products such as (III) besides fragmentation products, e.g. pyrazoles (IV) and dihydropyrazoles (V). The insertion products are isolated for the first time. This novel reaction may be regarded as a version of the Michael reaction enabling the preparation of β-ferrocenyl-β-hydrazinoketones as well as 1-hydrazinoalkyl-substituted ferrocene derivatives. -(KLIMOVA*, E. I.; VAZQUEZ LOPEZ, E. A.; MARTINEZ MENDOZA, J. M.; RUIZ RAMIREZ, L.; FLORES ALAMO, M.; BACKINOWSKY, L. V.; J. Heterocycl. Chem. 46 (2009) 3, 484-491; Fac. Quim., Univ. Natl. Auton. Mex., Coyoacan, 04510 Mexico, Mex.; Eng.) -H. Hoennerscheid 41-187

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The formation of 3‐ferrocenylpyrazole‐4‐carboxylates and alkylhydrazine insertion products from α‐ferrocenylmethylidene‐β‐oxocarboxylates

Klimova

Flores-Álamo

et al. 2011

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).The reactions of a-ferrocenylmethylidene-b-oxocarboxylates (1, 2, 3a, and 3b) with N-methyl-and N-(2-hydroxyethyl)hydrazines (5a, 5b) afford ethyl 1-alkyl-5-aryl(methyl)-3-ferrocenylpyrazole-4-carboxylates (6a-e) ($50%) and N-alkylhydrazine insertion products, viz., ethyl (N 0 -acyl-N 0 -alkylhydrazino)-3-ferrocenylpropanoates (7a-e) ($20%) and 1-acyl-2-(N 0 -alkyl-N 0 -ethoxycarbonylhydrazino)-2-ferrocenylethanes (8a-e) ($10%). The structures of the compounds obtained were established based on the spectroscopic data and X-ray diffraction analysis (for pyrazoles 6a and 6b).

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Insertion and fragmentation of 2‐ferrocenylmethylidene‐1, 3‐diketones upon their reactions with N‐methylhydrazine

Cited by 6 publications

References 18 publications

Cover Picture: Isolatable Organophosphorus(III)–Tellurium Heterocycles (Chem. Eur. J. 3/2014)

Cover Picture: Isolatable Organophosphorus(III)–Tellurium Heterocycles (Chem. Eur. J. 3/2014)

ChemInform Abstract: Insertion and Fragmentation of 2‐Ferrocenylmethylidene‐1,3‐diketones upon Their Reactions with N‐Methylhydrazine.

The formation of 3‐ferrocenylpyrazole‐4‐carboxylates and alkylhydrazine insertion products from α‐ferrocenylmethylidene‐β‐oxocarboxylates

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