Synthesis of New Furan-Derived N-Substitutedaminomethanephosphonates

Lewkowski, J.; Rzeźniczak, Monika; Skowroński, R.

doi:10.1080/00304940009356759

Cited by 14 publications

(14 citation statements)

References 10 publications

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“…The reaction proceeded much slower and moreover, the reaction did not go to completion. When other solvents (acetonitrile, diethyl ether, methanol 46 and toluene 47 ) were screened, methanol seemed to give the fastest reaction, without formation of any side products. Diethyl ether gave almost no reaction and acetonitrile resulted in the formation of side products.…”

Section: Introductionmentioning

confidence: 99%

Straightforward continuous synthesis of α-aminophosphonates under microreactor conditions

Meenen¹,

Moonen²,

Acke³

et al. 2005

Arkivoc

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The synthesis of α-aminophosphonates on a large scale is not always straightforward. One of the described methodologies has now been adjusted for use in a microreactor system. The CPC College System was used to investigate the continuous production of α-aminophosphonates. This technology couples miniaturisation to optimal reaction conditions for the production of chemical and pharmaceutical intermediates. The reaction of an imine with a dialkyl phosphite in different solvents was optimised, since the use of a solvent is necessary when using a microreactor. When methanol was used, a considerable reduction of the reaction time was noticed in comparison with other commonly used solvents. Subsequently, several reaction parameters were optimised in batch and compared with the continuous process in the microreactor. Similar yields and purities were obtained compared to the batch reaction. Using the microreactor system, the scale-up problems were avoided and large amounts of α-aminophosphonates could be generated in a short time.

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Section: Introductionmentioning

confidence: 99%

Straightforward continuous synthesis of α-aminophosphonates under microreactor conditions

Meenen¹,

Moonen²,

Acke³

et al. 2005

Arkivoc

View full text Add to dashboard Cite

show abstract

“…In our previous reports [6,8], the hypothetical reasons were proposed for the highly stereoselective addition of dialkyl phosphites to achiral terephthalic Schiff bases. This model may be also well adapted to the case of the similar addition of hypophosphorous acid.…”

Section: Resultsmentioning

confidence: 98%

“…However, it was proven in papers [2][3][4][5][6][7][8][9][10] that the addition of dialkyl or diaryl phosphites to N-alkyl terephthalic Schiff bases led to the exclusive formation of one diastereoisomeric form. Our previous study [6][7][8][9] revealed that this diastereoisomer was the meso form. On the other hand, the addition of dialkyl or diaryl phosphites to N-aryl terephthalic Schiff bases led exclusively either to the formation of the meso form or to both diastereomeric forms, which depended on the nature of the aryl substituent [8,9].…”

Section: Resultsmentioning

confidence: 99%

“…Schiff bases 2a-h were prepared following the published procedure [6] by the condensation of corresponding amines with terephthalic aldehyde 1 in methanol at room temperature. Corresponding imines were obtained in quantitative yields.…”

Section: Resultsmentioning

confidence: 99%

“…Later papers authored by Finocchiaro et al [2][3][4] and Gancarz et al [5] presented the discussion on the stereochemical aspect of these reactions. Our group has also contributed to this topic reporting about the stereochemistry of addition reactions to various N-substituted terephthalic imines [6][7][8][9]. A comprehensive and detailed report on NMR spectroscopic and molecular modeling studies of 1,4-phenylene-bis-aminomethane-bisphosphonates and related structures is given in [10].…”

Section: Introductionmentioning

confidence: 99%

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