Selective monodeoxygenation of certain quinoxaline 1,4-dioxides with trimethyl phosphite

Dirlam, John P.; McFarland, James W.

doi:10.1021/jo00428a020

Cited by 36 publications

(27 citation statements)

References 3 publications

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“…[17] The di-N-oxides were then selectively monodeoxygenated with trimethyl phosphite, as described by Dirlam and McFarland, [18] to yield the corresponding mono-N-oxides (1 and 2, Scheme 1). The products precipitated from the reaction mixture were isolated by suction filtration and recrystallized from methanol.…”

Section: Experimental Details Synthesis and Purificationmentioning

confidence: 99%

The enthalpies of dissociation of the NO bonds in two quinoxaline derivatives

Gomes

Monteiro

Campos

et al. 2008

J of Physical Organic Chem

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The present work reports the first experimental thermochemical study of mono-N-oxides derived from quinoxaline, namely, 3-methoxycarbonyl-2-methyl-quinoxaline N-oxide and 3-ethoxycarbonyl-2-methyl-quinoxaline N-oxide. The values of the enthalpies of formation, in the condensed state, and of the enthalpies of sublimation, derived from static bomb calorimetry and Calvet microcalorimetry measurements, respectively, are combined to derive the standard molar enthalpies of formation in the gaseous phase for these two compounds. From the latter values, the first and second N-O bond dissociation enthalpies for the corresponding di-N-oxides have been obtained. The gas-phase experimental results are also compared with calculated data obtained with a density functional theory approach.

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Section: Experimental Details Synthesis and Purificationmentioning

confidence: 99%

The enthalpies of dissociation of the NO bonds in two quinoxaline derivatives

Gomes

Monteiro

Campos

et al. 2008

J of Physical Organic Chem

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“…BFO's also react with β-diketone derivatives to form 2-acyl-quinoxaline 1,4-dioxides (6) [130,141,[144][145][146] and with β-ketoesters to give 2-carboxyalkyl derivatives (7) of Fig. (18) [131,[147][148][149][150]. Furthermore, 2-carboxamide derivatives (8) are obtained by condensation of BFO's with β-ketoamides of Fig.…”

Section: Anti-protozoal and Anti-candida Activitiesmentioning

confidence: 99%

“…The first synthon to be considered was the substituted enamine. A wide variety of enamines reacts with BFO's (1) involving a deamination to form QdNO's [128][129][130][131][132][133][134][135] or desilyation and deamination [129]. Variously substituted benzofurazan 1-oxide (1) gave 2-phenyl-quinoxalin 1,4-dioxides (2) of Fig.…”

Section: ) Conversion Of [124] Oxadiazolo [23-a] Quinoxalines To mentioning

confidence: 99%

Quinoxaline 1,4-Dioxide: A Versatile Scaffold Endowed With Manifold Activities

Carta

Corona²,

Loriga

2005

CMC

137

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Since 1940s, Quinoxaline 1,4-dioxides (QdNO's) are known as potent antibacterial agents, and subtherapeutic levels have been used to promote growth and improve efficiency of feed conversion in animal feed. They have also shown a selective cytotoxicity against hypoxic cells present in solid tumours. Furthermore, recent studies have put in evidence that QdNO's are endowed with antitubercular, antiprotozoal and anticandida activities. On the other hand, several authors have reported about photoallergic and mutagenic effects of some derivatives. QdNO's may also cause the development of antibiotic-resistant bacteria and influence the horizontal transfer of virulence genes between bacteria. In this review article we report the biological properties, the mode of action and Structure Activity Relationship (SAR) studies of the QdNO derivatives. Furthermore, some cytogenetic and genotoxic effects, classical and more recent method of synthesis, the quinoxaline 1,4-dioxides, and some of their most important reactions, were also reported.

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“…Following the procedure of Dirlam & McFarland (1977) ethyl-3-methyl-2-quinoxalinecarboxylate-1,4-dioxide (2.0 g, 8 mmol) (Robertson & Kasublck, 1973) was dissolved in 1-propanol (20 ml), trimethyl phosphate (2.0 g, 16 mmol) was added dropwise to the solution. The reaction mixture was heated under reflux for 2.5 h, and evaporated to dryness.…”

Section: Methodsmentioning

confidence: 99%

“…For the synthesis of the title compound, see: Dirlam & McFarland (1977 Table 1 Hydrogen-bond geometry (Å , ). …”

Section: Related Literaturementioning

confidence: 99%