Kinetics and mechanism of the Pudovik reaction in the azomethine series: III. Acid-catalyzed hydrophosphorylation of imines

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

doi:10.1134/s1070363206030121

Cited by 10 publications

(6 citation statements)

References 5 publications

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“…( E )-1-(1-Propenyl)-2-pyrrolidinone ( 7 ) was prepared according to the procedure described in the literature . All imines except 2a and 2n were prepared by refluxing a benzene solution of an equimolar mixture of the corresponding amine and aldehyde with a Dean–Stark trap for several hours . The crude products were purified by recrystallization or distillation.…”

Section: Methodsmentioning

confidence: 99%

“…32 All imines except 2a and 2n were prepared by refluxing a benzene solution of an equimolar mixture of the corresponding amine and aldehyde with a Dean−Stark trap for several hours. 33 The crude products were purified by recrystallization or distillation. Imine 2n was synthesized according to the procedure described in the literature.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Photochemically Promoted Aza-Diels–Alder-Type Reaction: High Catalytic Activity of the Cr(III)/Bipyridine Complex Enhanced by Visible Light Irradiation

Arai

Ohkuma

2017

J. Org. Chem.

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Aza-Diels-Alder-type cycloaddition reactions between a range of N-arylimines and functionalized alkenes were effectively catalyzed by the Cr(III)/bipyridine complex under irradiation of blue light, to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in high yields with excellent diastereoselectivity. Typically, the reaction of benzylideneaniline with 1-vinyl-2-pyrrolidinone proceeded smoothly with a substrate-to-catalyst molar ratio (S/C) of 1000 and completed within 4 h at room temperature (20-25 °C), affording the cycloaddition product in 97% yield.

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Section: Methodsmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Photochemically Promoted Aza-Diels–Alder-Type Reaction: High Catalytic Activity of the Cr(III)/Bipyridine Complex Enhanced by Visible Light Irradiation

Arai

Ohkuma

2017

J. Org. Chem.

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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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“…The hydrophosphorylation of Schiff bases with dialkyl phosphite, which can be considered as a Pudovik reaction applied to azomethines, or a Kabachnik-Fields reaction, can be performed in two separate steps with isolation of the intermediate imine, or in one pot, 24 all components being added at once, and in both cases the mechanism of this reaction remains unclear. 25,26 This hydrophosphorylation step was run in the presence of an excess of dimethyl phosphite used as solvent, as previously described for other PPH dendrimers in homogeneous conditions. 27 All materials were fully characterized by FTIR and 13 C, 31 P and 29 Si MAS NMR spectroscopies, which gave complementary information.…”

Section: Fig 2 and Esi3mentioning

confidence: 99%

PPH dendrimers grafted on silica nanoparticles: surface chemistry, characterization, silver colloids hosting and antibacterial activity

et al. 2013

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OATAO is an open access repository that collects the work of Toulouse researchers and makes it freely available over the web where possible. This is an author-deposited version published in : http://oatao.univ-toulouse.fr/ Eprints ID : 10069To link to this article : dendrimers grafted on silica nanoparticles: surface chemistry, characterization, silver colloids hosting and antibacterial activity. (2013) RSC Advances, vol. 3 (n° 41).Any correspondance concerning this service should be sent to the repository administrator: staff-oatao@listes-diff.inp-toulouse.fr PPH dendrimers grafted on silica nanoparticles: surface chemistry, characterization, silver colloids hosting and antibacterial activity3

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Kinetics and mechanism of the Pudovik reaction in the azomethine series: III. Acid-catalyzed hydrophosphorylation of imines

Cited by 10 publications

References 5 publications

Photochemically Promoted Aza-Diels–Alder-Type Reaction: High Catalytic Activity of the Cr(III)/Bipyridine Complex Enhanced by Visible Light Irradiation

Photochemically Promoted Aza-Diels–Alder-Type Reaction: High Catalytic Activity of the Cr(III)/Bipyridine Complex Enhanced by Visible Light Irradiation

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

PPH dendrimers grafted on silica nanoparticles: surface chemistry, characterization, silver colloids hosting and antibacterial activity

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