A study on the michael addition of dialkylphosphites to methylvinylketone

Keglevich, György; Sipos, Melinda; Takács, Daniella; Greiner, István

doi:10.1002/hc.20266

Cited by 52 publications

(27 citation statements)

References 17 publications

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“…There was no need to apply MW irradiation [55]. Phospha-Michael reactions of methyl vinyl ketone with P-heterocyclic nucleophiles deriving from a dibenzo-1,2-oxaphosphorine oxide or 1,3,2-dioxaphosphorine oxide were carried out in the presence of DBU [56].…”

Section: Phospha-michael Additionsmentioning

confidence: 99%

The Use of MW in Organophosphorus Chemistry

Keglevich

Bálint²,

Kiss

2016

SpringerBriefs in Molecular Science

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The third chapter summarizes a special field, the application of the microwave (MW) technique in the synthesis of organophosphorus compounds. On the one hand, reactions are shown that are otherwise rather reluctant on traditional thermal heating. On the other hand, reactions are discussed, which, became more efficient (shorter reaction times and higher yields) on MW irradiation. Finally, the simplification of catalytic systems under MW conditions are surveyed.

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Section: Phospha-michael Additionsmentioning

confidence: 99%

The Use of MW in Organophosphorus Chemistry

Keglevich

Bálint²,

Kiss

2016

SpringerBriefs in Molecular Science

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“…Recently, various methodologies have been developed for the synthesis of heteroaryl/aryl/alkyl α-hydroxyphosphonates by using Lewis acid or alumina, 11 Lewis bases 12 (Et 3 N, pyridine and TMG) and strong bases 13 (NaH, n-BuLi, and LDA). In addition, some catalyst or promoters, including metal oxides (such as Al 2 O 3 14 and MgO), Bronsted bases (EtONa and Ti(OiPr) 4 ), 15,16 and some others like KF and MoO 2 Cl 2 17,18 were found to be effective for this transformation. However, some disadvantages associated with these reported procedures are addition of the supplementary reagents like MgCl 2 /Et 3 N 19a and In/AcOH, 19b high heating, long reaction time, 18 costly, and moisture sensitive catalysts and also tedious work up processes to remove catalyst.…”

Section: Introductionmentioning

confidence: 98%

Ultrasonicated, Nano-ZnO Catalyzed Green Synthesis of α-Hydroxyphosphonates and their Antioxidant Activity

Basha

Syed

Sekhar

et al. 2014

Phosphorus, Sulfur, and Silicon and the Related Elements

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A green method was developed for the synthesis of 12 α-hydroxyphosphonates 3a-l through the Pudovik reaction of diethyl phosphite (2) and aromatic/heterocyclic aldehydes 1a-l under sonication and conventional conditions using ZnO nano sheets as a catalyst. The advantages of this protocol are high yields, high purity of the desired products, short reaction times, easy workup, and reusability of the catalyst. The structure of the catalyst, ZnO nano sheets, was elucidated by EDS, TEM, XRD, and IR and the title compounds were characterized by spectral data (IR, 1 H, 13 C, 31 P NMR, and mass spectrometry) and elemental analysis. The title compounds were screened for their radical scavenging activity employing DPPH, H 2 O 2 methods and IC 50 values also determined. Compounds 3i, 3j, 3k, and 3l were exhibited promising antioxidant activity almost equal to standard BHT.

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“…In our laboratory, the possible accomplishments of the phosphaMichael reaction were studied on simple model reactions [4]. The addition of >P(O)H species to α-methyleneglutaric esters was performed to make available potential NAALADase inhibitors useful in the treatment of stroke [5].…”

Section: Introductionmentioning

confidence: 99%

Phospha‐michael reactions involving p‐heterocyclic nucleophiles

Keglevich

Sipos

Takács

et al. 2008

Heteroatom Chemistry

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P-heterocyclic γ-ketophosphonateswere synthesized by the Michael reaction of methyl vinyl ketone with dibenzo-1,2-oxaphosphorine 2-oxide, 1,3,2-dioxaphosphorine 2-oxide and benzo-1,3,2-dioxaphospholane 2-oxide, respectively. In the first two cases, 50% of 1,8-diazabicyclo[5.4.0]undec-7-ene had to be used that was also required in the addition of dibenzooxaphosphorine oxide to cyclohexenone to result in the formation of the corresponding γ-ketophosphonate. The addition of dibenzooxaphosphorine oxide to less reactive 1,2-dihydrophosphinine oxide was accomplished after activation by an equimolar amount of trimethylaluminum to afford a 3-P(O)<-1,2,3,6-tetrahydrophosphinine oxide, which was subjected to catalytic hydrogenation to provide the corresponding 1,2,3,4,5,6-hexahydrophosphinine oxide.

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A study on the michael addition of dialkylphosphites to methylvinylketone

Cited by 52 publications

References 17 publications

The Use of MW in Organophosphorus Chemistry

The Use of MW in Organophosphorus Chemistry

Ultrasonicated, Nano-ZnO Catalyzed Green Synthesis of α-Hydroxyphosphonates and their Antioxidant Activity

Phospha‐michael reactions involving p‐heterocyclic nucleophiles

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