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Microwave-Assisted Kabachnik⁻Fields Reaction with Amino Alcohols as the Amine Component.

ABSTRACT: In this paper, the microwave (MW)-assisted catalyst-free and mostly solvent-free Kabachnik-Fields reaction of amino alcohols, paraformaldehyde, and various >P(O)H reagents (dialkyl phosphites, ethyl phenyl-H-phosphinate, and secondary phosphine oxides) is reported. The synthesis of N-2-hydroxyethyl-α-aminophosphonate derivatives was optimized in respect of the temperature, the reaction time, and the molar ratio of the starting materials. A few by-products were also identified. N,N-Bis(phosphinoylmethyl)amines containing a hydroxyethyl group were also prepared by the double Kabachnik-Fields reaction of ethanolamine with an excess of paraformaldehyde and secondary phosphine oxides. The crystal structure of a 2-hydroxyethyl-α-aminophosphine oxide and a bis(phosphinoylmethyl)ethanolamine was studied by X-ray analysis.

SUBMITTER: Tajti A

PROVIDER: S-EPMC6514811 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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Microwave-Assisted Kabachnik⁻Fields Reaction with Amino Alcohols as the Amine Component.

Tajti Ádám Á Szatmári Enikő E Perdih Franc F Keglevich György G Bálint Erika E

Molecules (Basel, Switzerland) 20190425 8

In this paper, the microwave (MW)-assisted catalyst-free and mostly solvent-free Kabachnik-Fields reaction of amino alcohols, paraformaldehyde, and various >P(O)H reagents (dialkyl phosphites, ethyl phenyl-H-phosphinate, and secondary phosphine oxides) is reported. The synthesis of N-2-hydroxyethyl-α-aminophosphonate derivatives was optimized in respect of the temperature, the reaction time, and the molar ratio of the starting materials. A few by-products were also identified. N ...[more]

PMID: 31027303

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