Synthesis of Aliphatic 1,3-Dinitro Compounds

Alcantara, M.‐P. Derri; Cabrera‐Escribano, Francisca; Gómez-Sánchez, Antonio; Diánez, M. J.; Estrada, M. D.; López-Castro, A.; Pérez-Garrido, Simeón

doi:10.1055/s-1996-4150

Cited by 31 publications

(15 citation statements)

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“…[15] As ide reactionr elated to that in which the 2-aryl-1,3-dinitro compounds can be readily transformed under basic conditions into 2-isoxazoline-2-oxides or isoxazoles has been reported. [18,19] In our case, the formation of the 3,5-dimethyl-4-arylisoxazole byproduct was also observeda nd this was minimized by adding acetic acid. The bestr eaction conditions provided the pyrazoles in 65 %y ield.…”

Section: Synthesissupporting

confidence: 50%

“…In the third step, the Michael addition of nitroethane to the nitroalkene occurreda tr oom temperature for the C 10 and at 50 8Cf or the C 14 derivatives owing to the lows olubility of the latter in nitroethane. The 1,3-dinitroalkane product is not unique but am ixture of four stereoisomers [18] owing to the formation of two stereogenic centers (a dl pair and two meso forms for 3a-d and 3f,a nd four diastereoisomers for 3e), which appear on at hin layer chromatography (TLC) plate as three spots. These componentsc ould be isolated and characterized by 1 HNMR spectroscopy ( Figure S1 in the Supporting Information).…”

Section: Synthesismentioning

confidence: 99%

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Supramolecular Columnar Liquid Crystals with Tapered‐Shape Simple Pyrazoles Obtained by Efficient Henry/Michael Reactions

Blanco

Iguarbe

Barberá

et al. 2016

Chemistry A European J

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A straightforward synthesis of mesogenic pyrazoles starting from benzaldehydes by a combination of efficient Henry and Michael reactions led to novel supramolecular liquid crystals. The mesogens are fluorescent 3,5-dimethyl-4-(di or trialkoxyphenyl)pyrazoles and, in spite of the tapered shape of these molecules and their structural simplicity (only one phenyl ring), columnar liquid-crystal phases were formed that are stable at room temperature. The self-assembled structure was studied by XRD and the columnar cross section contains two molecules on average with an antiparallel arrangement of pyrazoles interacting through hydrogen bonds. In contrast, the single-crystal structure of a trimethoxy analog did not show hydrogen-bonded pyrazoles but chains of head-to-tail arranged molecules.

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Section: Synthesissupporting

confidence: 50%

Section: Synthesismentioning

confidence: 99%

Supramolecular Columnar Liquid Crystals with Tapered‐Shape Simple Pyrazoles Obtained by Efficient Henry/Michael Reactions

Blanco

Iguarbe

Barberá

et al. 2016

Chemistry A European J

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“…[33][34][35][36] The mechanism of their formation was assumed to be a three-step base-catalysed reaction as follows: (1) nitroaldol addition to form the nitroalcohol;…”

Section: Resultsmentioning

confidence: 99%

Nitroaldol-reaction of aldehydes in the presence of non-activated Mg:Al 2:1 hydrotalcite; a possible new mechanism for the formation of 2-aryl-1,3-dinitropropanes

et al. 2005

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“…1,3 Dinitropropane (1a) 11 and aryl substituted 1,3 dinitro propanes 1b-d 12 and 2,2 dimethyl 1,3 dinitropropane (1e) 13 were synthesized according to described procedures. The physi cochemical constants of compounds 3a 5 (eluent petroleum ether-CHCl 3 , 1 : 3), 3d 7 (eluent CНCl 3 -Pr i OH, 7 : 3), 3g 7 (eluent CНCl 3 -Pr i OH, 9 : 1), and 5 14 (eluent CНCl 3 -Pr i OH, 1 : 9) coincided with published data.…”

Section: Methodsmentioning

confidence: 99%

One-step synthesis of substituted 3,5-dinitropiperidines and 1,5-dinitro-3,7-diazabicyclo[3.3.1]nonanes from 1,3-dinitropropanes

et al. 2005

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1,5 Dinitro 3,7 diazabicyclo[3.3.1]nonane derivatives were synthesized in up to 83% yields by the Mannich reaction of 1,3 dinitropropanes with excess formaldehyde and primary amines. In some cases, for instance, when 2,2 dimethyl 1,3 dinitropropane and benzylamine or monoethanolamine are used, the reaction occurs with low yields or stops at the step of forma tion of 3,5 dinitropiperidines. The influence of the structure of the starting compounds and reaction conditions on the yields of 1,5 dinitro 3,7 diazabicyclo[3.3.1]nonanes and 3,5 dinitropiperidines was studied.

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Synthesis of Aliphatic 1,3-Dinitro Compounds

Cited by 31 publications

References 0 publications

Supramolecular Columnar Liquid Crystals with Tapered‐Shape Simple Pyrazoles Obtained by Efficient Henry/Michael Reactions

Supramolecular Columnar Liquid Crystals with Tapered‐Shape Simple Pyrazoles Obtained by Efficient Henry/Michael Reactions

Nitroaldol-reaction of aldehydes in the presence of non-activated Mg:Al 2:1 hydrotalcite; a possible new mechanism for the formation of 2-aryl-1,3-dinitropropanes

One-step synthesis of substituted 3,5-dinitropiperidines and 1,5-dinitro-3,7-diazabicyclo[3.3.1]nonanes from 1,3-dinitropropanes

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