The formation of dimethyl amino(pyrene-1-yl)methylphosphonates in the Kabachnik-Fields reaction with dibenzyl phosphite, pyrene-1-carboxaldehyde and a non-aromatic amine in methanol

Lewkowski, J.; Moya, Maria Rodriguez

doi:10.1080/10426507.2017.1308932

Cited by 6 publications

(3 citation statements)

References 23 publications

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“…The catalyst-free conversion of pyrene-1-carboxaldehyde ( 56 ) to the corresponding α-aminophosphonate ( 57 ) in reaction with amines ( 55 ) and dibenzyl phosphite is noteworthy ( Scheme 43 ) [ 67 ]. It was observed that the corresponding α hydroxyphosphonate ( 58 ) was also present in the mixture formed as an intermediate in the Pudovik reaction.…”

Section: Kabachnik–fields Reactions With Dialkyl Phosphites Alkyl H -Phosphinates and Secondary Phosphine Oxidesmentioning

confidence: 99%

Synthesis of α-Aminophosphonates and Related Derivatives; The Last Decade of the Kabachnik–Fields Reaction

Varga

Keglevich

2021

Molecules

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The Kabachnik–Fields reaction, comprising the condensation of an amine, oxo compound and a P-reagent (generally a >P(O)H species or trialkyl phosphite), still attracts interest due to the challenging synthetic procedures and the potential biological activity of the resulting α-aminophosphonic derivatives. Following the success of the first part (Molecules 2012, 17, 12821), here we summarize the synthetic developments in this field accumulated in the last decade. The procedures compiled include catalytic accomplishments as well as catalyst-free and/or solvent-free “greener” protocols. The products embrace α-aminophosphonates, α-aminophosphinates, and α-aminophosphine oxides along with different bis derivatives from the double phospha-Mannich approach. The newer developments of the aza-Pudovik reactions are also included.

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Section: Kabachnik–fields Reactions With Dialkyl Phosphites Alkyl H -Phosphinates and Secondary Phosphine Oxidesmentioning

confidence: 99%

Synthesis of α-Aminophosphonates and Related Derivatives; The Last Decade of the Kabachnik–Fields Reaction

Varga

Keglevich

2021

Molecules

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“…It was not easy to achieve selectivity. At the same time, it is known that the benzyl phosphonates may undergo easy substitution of the BnO group [29]. For this, alcoholysis of dibenzyl phosphite (3) seemed to be an appropriate model.…”

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

confidence: 99%

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

2020

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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.

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“…Both the alcoholysis of phosphinates [10] and that of phosphonates [11] have been studied by the senior author of this paper and Kosolapoff, respectively. The transesterification of dialkyl phosphites (H-phosphonates) was investigated by different groups headed, among others, by Aitken and Lewkowski [11][12][13][14]. The two-step transformations of dialkyl phosphites were also performed under MW conditions [15,16].…”

Section: Introductionmentioning

confidence: 99%

Alcoholysis Versus Fission of the Ester Group During the Reaction of Dialkyl Phenylphosphonates in the Presence of Ionic Liquids

Harsági

Bertha

Kiss

et al. 2021

COC

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: In the microwave-assisted alcoholysis of dialkyl phenylphosphonates performed in the presence of suitable ionic liquids, such as [bmim][BF4] or [bmim][PF6] affording the phosphonate with mixed alkoxy groups and the fully transesterified product, the fission of the phosphonate function to the ester-acid or diacid moiety was inevitable. Moreover, in the presence of [emim][HSO4], the reaction could be performed to afford the phosphonic ester-acid with a selectivity of 66% and the diacid in a selectivity of 97%. The ester-acids provided by the new protocol may be valuable intermediates.

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The formation of dimethyl amino(pyrene-1-yl)methylphosphonates in the Kabachnik-Fields reaction with dibenzyl phosphite, pyrene-1-carboxaldehyde and a non-aromatic amine in methanol

Cited by 6 publications

References 23 publications

Synthesis of α-Aminophosphonates and Related Derivatives; The Last Decade of the Kabachnik–Fields Reaction

Synthesis of α-Aminophosphonates and Related Derivatives; The Last Decade of the Kabachnik–Fields Reaction

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

Alcoholysis Versus Fission of the Ester Group During the Reaction of Dialkyl Phenylphosphonates in the Presence of Ionic Liquids

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