Chemistry of the Aliphatic Polynitro Compounds and Their Derivatives

Noble, Paul N.; Borgardt, F. G.; Reed, Wilmer L.

doi:10.1021/cr60227a003

Cited by 57 publications

(19 citation statements)

References 85 publications

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“…Their IR spectra are characterized by a certain shift of the absorption bands from the asymmetrical stretching vibrations of the trinitromethyl fragment to the high-frequency region (16001640 cm 1 ) with respect to the spectra of the other aliphatic polynitro derivatives (15971603 cm 1 ) [10]. This phenomenon was previously observed for pentanitroethyl compounds and hexanitroethane (1595 1636 cm 1 ) [6]: therewith in the latter spectra a strong dublet was observed in this region.…”

supporting

confidence: 55%

Nitration of Triazolyl-substituted Ketones

et al. 2005

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supporting

confidence: 55%

Nitration of Triazolyl-substituted Ketones

et al. 2005

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“…The reaction of methyl nitroacetate 1 with isopropylamine 4 and formaldehyde in methanol (Scheme 2) gives the expected hexahydropyrimidine 8 along with the 5-hydroxymethyl-5-nitrohexahydropyrimidine (9) in 35 and 17% yield respectively. The nitro alcohol 9 is likely formed as a result of hydrolysis and decarboxylation of compound 8 and subsequent reaction of the 1,3-diisopropyl-5-nitrohexahydropyrimidine (10) formed with a molecule of formaldehyde via a Henry reaction [21,22]. The structure of the hexahydropyrimidine 9 was identified from 1 H and 13 C NMR spectroscopic data.…”

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confidence: 99%

Methyl nitroacetate and 3-nitropropionate in the synthesis of hexahydropyrimidines and piperidines

Shakirov

Dokichev

Biglova

et al. 2008

Chem Heterocycl Comp

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Treatment of methyl nitroacetate and 3-nitropropionate with formaldehyde and primary amines underMannich reaction conditions gives 5-nitrohexahydropyrimidines. In the case of methyl nitroacetate both the 5-nitrohexahydropyrimidine and isomeric 3,5-di(methoxycarbonyl)-1-methyl-3,5-dinitropiperidines are formed.The reaction of primary amines and formaldehyde with compounds containing a mobile hydrogen atom on a carbon atom is widely used in organic synthesis as a convenient method for preparing tetrahydro-1,3-oxazines, hexahydropyrimidines [1, 2], and also 3-aza-[3-6] and 3,7-diazabicyclo[3,3,1]nonanes [3,[7][8][9][10][11][12][13][14][15]. Members of this class of compounds show high physiological activity and are used in medical practice as antimicrobial, antiviral, antitumor and other medicinal agents [10][11][12]16]. It is known that nitro-substituted heterocyclic compounds show increased antibacterial activity [1], can behave as sources of nitric oxide [17] in the human organism, and they are of interest both as chemotherapeutic agents and as intermediates in organic synthesis. Hence 5-[2-(methoxycarbonyl)ethyl]-1,3-dimethyl-5-nitrohexahydropyrimidine shows clear antiarrythmic activity [18] and trinitrohexahydropyrimidine (containing a glutaric acid fragment) is a convenient synthon for preparing immunologically active peptide conjugates [19] used in immunoenzymic analysis.Condensation with a nitro compound has shown promise in the synthesis of novel, practically important polyfunctional six-membered nitrogen heterocycles. According to literature data the course of the reaction of aliphatic mononitroalkanes with formaldehyde and primary amines depends on the structure of the starting reagents, their ratio, the temperature, and the nature of the solvent and it can occur to form amines, diaminopropanes, tetrahydrooxazines, and hexahydropyrimidines [1,2]. It has been shown previously that the reaction of methyl 4-nitrobutanoate with methylamine hydrochloride and CH 2 O occurs in 40% yield to give 5-nitro-5-[2-(methoxycarbonyl)ethyl]-1,3-dimethyl-hexahydropyrimidine and it is formed exclusively via the CH 2 NO 2 fragment of the starting nitrobutanoate [18].

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“…[7][8][9] Used in nitration previously unknown N (ω acylami no β,β dinitroalkyl)tetrahydro 1,3 oxazines and N (ω acylamino β,β dinitroalkyl)oxazolidines 3a-e were pre pared under conditions similar to those for a 1,1 dinitro ethane derivative 2 (Scheme 3).…”

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confidence: 99%