Microwave‐assisted phospha‐michael addition of dialkyl phosphites, a phenyl‐<i>H</i>‐phosphinate, and diphenylphosphine oxide to maleic derivatives

Bálint, Erika; Takacs, J. M.; Drahos, László; Keglevich, György

doi:10.1002/hc.21007

Cited by 28 publications

(14 citation statements)

References 22 publications

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“…[89] Under microwave assisted irradiation, N-substituted maleimides 78 reacted with (RO) 2 POH to produce 3-(dialkoxyphosphonyl)succinimide derivatives 79 (Scheme 32). [90] In a different trial, 1,5,7-triazabicyclo[4.4.0]dec-5-ene [TBD] was used as a catalyst. [91] In the same fashion, 1,4-unsaturated amides 80 reacted with DMP to afford the regioselective phosphonylated products 81.…”

Section: Reactions With Amides Imides and Thioamidesmentioning

confidence: 99%

Investigations of the Chemistry of Alkyl Phosphites Toward Nitrogen-Containing Compounds: Efficient Approaches to α-Amino-, β-Amino-, and/or Enaminophosphonates

Abdou

Barghash

Bekheit

2015

Synthetic Communications

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In this study, we report recent investigations of the chemical reactivity of alkyl phosphites mainly trialkyl and dialkyl phosphites with molecules containing different nitrogen-containing compounds reported by us and other research groups over the last twenty five years. Earlier leader important reports were also considered. The reviewed investigations in this article are customized, only according to the type of the nitrogenfunctional groups: [amines (primary, secondary, and tertiary amines), imines, amides, thioamides, nitriles, isocyanates, isothiocyanates, oximes, hydrazones, diazo, and azides]and not according to the site of attack or the final products. Furthermore, the present review article focuses on the synthesis of α-amino-, β-amino-and/or enaminophosphonates. These compounds occupy an important role in pharmaceutical chemistry.2 GRAPHICAL ABSTRACT:

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Section: Reactions With Amides Imides and Thioamidesmentioning

confidence: 99%

Investigations of the Chemistry of Alkyl Phosphites Toward Nitrogen-Containing Compounds: Efficient Approaches to α-Amino-, β-Amino-, and/or Enaminophosphonates

Abdou

Barghash

Bekheit

2015

Synthetic Communications

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“…MW addition promoted the addition of dialkyl phosphites, ethyl phenyl-Hphosphinate and diphenylphosphine oxide to the reactive unsaturation of N-phenyl and N-methylmaleimide, as well as maleic anhydride (Schemes 3.27 and 3.28) [60]. In most cases, the reactions were performed in the absence of any solvent.…”

Section: -86%mentioning

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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“…The MW-assisted phospha-Michael reaction was then extended to the addition of dialkyl phosphites, a phenyl-H-phosphinate and diphenylphosphine oxide to maleic derivatives, N-substituted maleimide, and maleic acid anhydride giving rise to >P(O)-substituted succinic derivatives (38 and 39) (Scheme 13) [58].…”

Section: Phospha-michael Reactionsmentioning

confidence: 99%