2002
DOI: 10.1021/jo026275+
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Iminopropadienones from Dioxanediones, Isoxazolopyrimidinones, Pyridopyrimidinones, and Pyridopyrimidinium Olates

Abstract: Iminopropadienones, RN=C=C=C=O, can be generated from four different types of precursors in flash vacuum thermolysis reactions: 1,3-dioxane-4,6-diones 1, isoxazolopyrimidinones 2, pyridopyrimidinium olates 3, and pyridopyrimidinones 4. 2,6-Difluorophenyl-, 2,6-diethylphenyl-, o-tert-butylphenyl-, and mesityliminopropadienone have been directly observed by Ar matrix IR spectroscopy in one or more of these reactions. Reactions with bis-nucleophiles afford pyridopyrimidinones and perhydrodiazepinone derivatives.

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Cited by 21 publications
(13 citation statements)
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“…[1][2][3][4] These unusual cumulenes have been characterized by IR and NMR spectroscopy [1][2][3][4][5] as well as by their chemical reactions. Iminopropadienones 4 undergo a multitude of nucleophilic addition reactions; with bisnucleophiles, cyclization leads to a variety of heterocyclic compounds containing 5-, 6-, 7-, 8-, and 9-membered rings.…”
Section: Introductionmentioning
confidence: 99%
See 1 more Smart Citation
“…[1][2][3][4] These unusual cumulenes have been characterized by IR and NMR spectroscopy [1][2][3][4][5] as well as by their chemical reactions. Iminopropadienones 4 undergo a multitude of nucleophilic addition reactions; with bisnucleophiles, cyclization leads to a variety of heterocyclic compounds containing 5-, 6-, 7-, 8-, and 9-membered rings.…”
Section: Introductionmentioning
confidence: 99%
“…2,4,6 Thus, in particular, the 2-pyridyl-and 2,6-difluorophenyliminopropadienones afford significant amounts of "abnormal" products apparently arising from initial attack of the strongest nucleophilic center of the bisnucleophile on the CdN group, or from attack of the weaker nucleophilic center on the CdO group. 2,4,6 The addition of tertiary and secondary amines to aryliminopropadienones has been examined by low temperature IR spectroscopy. 7 Tertiary amines (trimethylamine) add to the CdO group to form ketenimine-type zwitterionic intermediates in all cases.…”
Section: Introductionmentioning
confidence: 99%
“…However, some iminopropadienones are isolable at room temperature, and this has allowed the recording of 13 C NMR spectra in several cases . They are mostly generated by flash vacuum thermolysis (FVT) from precursors such as 1,3-dioxane-4,6-diones (Meldrum’s acid derivatives) and isoxazolopyrimidinone derivatives. We have investigated the reactivity of the iminopropadienones with different amines, viz. DMA, diethylamine (DEA), and TMA.…”
Section: Introductionmentioning
confidence: 99%
“…Therefore, in this series, species 3 [R = N−C­(NH)­NH 2 ] is predicted to be the most flexible molecule in the OCCCN plane and suggests its high tendency to cyclization. Other works have shown the electrophilic character of the CO group of iminopropadienones reacting with amines and alcohol . In particular, Aly and Nour-El-Din pointed out that cyclization is a very important reaction of amidines, leading to various heterocyclic compounds, including pyrimidines …”
Section: Resultsmentioning
confidence: 99%