Synthesis of Ethyl Octyl α-Aminophosphonate Derivatives

Tajti, Ádám; Bálint, Erika; Keglevich, György

doi:10.2174/1570179413666151218202757

Cited by 20 publications

(18 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The formation of 6% of the N -methylated by-product 3 {δ p (CDCl 3 ) 25.4, [M + H] + found = 286.1582, C 14 H 25 NO 3 P requires 286.1567} was inevitable (Table 1, entries 3 and 4). Similar N -methylations have been observed also in other cases [59–60]. At 80 °C, diethyl phosphite (DEP) was less reactive than DMP, as after an irradiation time of 1 h, the conversion was only 76% (Table 1, entry 5).…”

Section: Resultssupporting

confidence: 81%

The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction

Bálint¹,

Tajti

Ádám

et al. 2017

Beilstein J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

A family of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides was synthesized by the microwave-assisted solvent-free addition of dialkyl phosphites and diphenylphosphine oxide, respectively, to imines formed from benzaldehyde derivatives and primary amines. After optimization, the reactivity was mapped, and the fine mechanism was evaluated by DFT calculations. Two α-aminophosphonates were subjected to an X-ray study revealing a racemic dimer formation made through a N–H···O=P intermolecular hydrogen bridges pair.

show abstract

Section: Resultssupporting

confidence: 81%

The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction

Bálint¹,

Tajti

Ádám

et al. 2017

Beilstein J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…We elaborated a simple method for the preparation of α‐aminophosphonates with a mixed ester functionality by the MW‐assisted condensation of amines, paraformaldehyde, and ethyl octyl phosphite . As a continuation, in this paper, the synthesis of species containing the ‐NHCH 2 P(O)PhOR moiety is described.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of alkyl α‐aminomethyl‐phenylphosphinates and N,N‐bis(alkoxyphenylphosphinylmethyl)amines by the microwave‐assisted Kabachnik–Fields reaction

Bálint¹,

Tóth

Keglevich

2016

Heteroatom Chemistry

Self Cite

View full text Add to dashboard Cite

As a novel extension, the Kabachnik–Fields reaction was applied to the synthesis of alkyl α‐aminomethyl‐phenylphosphinates, and the double phospha‐Mannich reaction was utilized in the preparation of bis(alkoxyphenylphosphinylmethyl)amines. A total of 27 new aminophosphinate derivatives were synthesized by the microwave‐assisted solvent‐free condensation of alkyl phenyl‐H‐phosphinates, paraformaldehyde, and primary or secondary amines. The starting P‐species were also prepared under microwave conditions. The formation of the N‐methylated aminomethyl‐phenylphosphinate by‐products was also investigated.

show abstract

“…Keglevich and co-workers have investigated the MW-assisted transesterifications (alcoholyses) of dialkyl phosphites [27,28]. These kinds of reactions take place in two steps resulting first in a phosphite with two different alkyl groups, and in the second step the fully transesterified dialkyl phosphite.…”

Section: Mw-assisted Transesterification Of Dibenzyl Phosphite (3)mentioning

confidence: 99%

“…It was found that alkylation was more suitable to convert the second hydroxy group into an alkoxy unit [26]. The senior author of this article together with co-workers developed the MW-assisted transesterification (alcoholysis) of dialkyl phosphites [27,28]. It was possible to conduct the reactions to afford the dialkyl phosphites with two different alkyl groups as the predominating products.In this article we summarize our experience acquired during the translation of batch MW preparations of H-phosphinates and H-phosphonates into flow processes.…”

mentioning

confidence: 99%

Continuous Flow Esterification of a H-Phosphinic Acid, and Transesterification of H-Phosphinates and H-Phosphonates under Microwave Conditions

2020

Self Cite

View full text Add to dashboard Cite

The microwave (MW)-assisted direct esterification of phenyl-H-phosphinic acid, transesterification of the alkyl phenyl-H-phosphinates so obtained, and the similar reaction of dibenzyl phosphite (DBP) were investigated in detail, and the batch accomplishments were translated into a continuous flow operation that, after optimization of the parameters, such as temperature and flow rate, proved to be more productive. Alcoholysis of DBP is a two-step process involving an intermediate phosphite with two different alkoxy groups. The latter species are of synthetic interest, as precursors for optically active reagents.

show abstract

Synthesis of Ethyl Octyl α-Aminophosphonate Derivatives

Cited by 20 publications

References 0 publications

The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction

The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction

Synthesis of alkyl α‐aminomethyl‐phenylphosphinates and N,N‐bis(alkoxyphenylphosphinylmethyl)amines by the microwave‐assisted Kabachnik–Fields reaction

Continuous Flow Esterification of a H-Phosphinic Acid, and Transesterification of H-Phosphinates and H-Phosphonates under Microwave Conditions

Contact Info

Product

Resources

About