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Sobanov, A. A.; Zolotukhin, A. V.; Галкин, В. И.; Черкасов, Р. А.; Pudovik, A. N.

doi:10.1023/a:1020794530963

Cited by 11 publications

(8 citation statements)

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“…34 In a following experiment, the methanol and dimethyl phosphite were purified prior to use in order to establish the need of acid catalysis, originating from a small degree of hydrolysis of the phosphite reagent. 45 Therefore, sodium metal was added to the reagents prior to distillation.…”

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

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“…The reaction starts with the addition of one equivalent of dialkyl H‐phosphonate to the imine 4 , most likely following a mechanism discussed by the Pudovik group 38–40. As an intermediate the phosphonate 5 is formed, formally an imino‐substituted aminomethane phosphonic acid dialkyl ester, containing the N=CH–C(P)–N skeleton.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, NMR‐Spectroscopy, and Molecular Structure of a Phosphonyl Ene Diamine

Bogomilova

Günther

Hägele

et al. 2011

Zeitschrift anorg allge chemie

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First examples of ene diamines with a phosphonate function at the C=C double bond were obtained by the reaction of dialkyl Hphosphonates with bis(N-tert-butyl)-diimine derived from glyoxal, [1,4-bis(tert-butyl)-1,4-diaza-1,3-butadiene], and isolated as hydrochlorides. Preferentially the cis-diamine is formed. The new phosphonates are characterized by multinuclear NMR spectroscopy( 1 H, 13 C, * Dr. A. Bogomilova Fax: +359-2-870-0309 E-Mail: anitabogomilova@abv.bg [a] Institute of Polymers 1213 31 P).In addition the methyl ester 8a was characterized by 14,15 N NMR spectroscopy as well as by several 2D NMR techniques and singlecrystal X-ray diffraction, unequivocally establishing the ene diamine structure. In the crystal dimers of the cations are formed by P-O···H-N hydrogen bonding.

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“…Furthermore, it has been demonstrated that dialkyl phosphite itself is able to convert imines into the corresponding 1‐aminoalkyl phosphonates with complete 1,2‐regioselectivity 2. 13 However, in a sufficiently acidic medium, dialkyl trimethylsilyl phosphite is able to convert α,β‐unsaturated imines 5 into diphosphonates 6 in one step through a sequential tandem 1,4–1,2‐addition (pathway A of Scheme ) 15. As the free phosphonic acids of diphosphonates16 are potential Glu agonists or antagonists, our future research will be directed towards the synthesis of enantiopure PAP derivatives 17…”

Section: Methodsmentioning

confidence: 99%

One‐Pot Tandem 1,4–1,2‐Addition of Phosphites to α,β‐Unsaturated Imines for the Synthesis of Glutamic Acid Analogues

Moonen¹,

Meenen²,

Verwée³

et al. 2005

Angewandte Chemie

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Cited by 11 publications

References 1 publication

Straightforward continuous synthesis of α-aminophosphonates under microreactor conditions

Straightforward continuous synthesis of α-aminophosphonates under microreactor conditions

Synthesis, NMR‐Spectroscopy, and Molecular Structure of a Phosphonyl Ene Diamine

One‐Pot Tandem 1,4–1,2‐Addition of Phosphites to α,β‐Unsaturated Imines for the Synthesis of Glutamic Acid Analogues

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