Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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    Cycloalkenopyridines by ring transformations of diazines and triazines
    Plas, H.C. van der - \ 2008
    ARKIVOC 2008 (2008)iii. - ISSN 1551-7004 - p. 127 - 139.
    diels-alder reactions - cyclo-addition reaction - 2,2'-bipyridine ligands - organic-synthesis - 1,2,4-triazines - enamines - 5,5'-bi-1,2,4-triazines - 1,2,3-triazine - alkaloids - route
    This paper is a short review on the synthesis of 2,3-cycloalkenopyridines and 3,4-cycloalkenopyridines by inter- and intra-molecular cycloadditions.
    Oxidative amino-dehydrogenation of azines
    Plas, H.C. van der - \ 2004
    Advances in Heterocyclic Chemistry 86 (2004). - ISSN 0065-2725 - p. 1 - 40.
    ammonia-potassium-permanganate - sigma-adduct formation - nuclear-magnetic-resonance - liquid-ammonia - heterocyclic-systems - nucleophilic-substitution - naphthyridine chemistry - chichibabin amination - covalent amination - effective reagent
    This chapter reviews the oxidative amino-dehydrogenation reactions. It focuses on reactions in which a substrate reacts with an aminating agent in the presence of an oxidant. This amination methodology is very useful to replace ring hydrogens in highly electron-deficient azaheterocycles by an amino, alkylamino, dialkylamino, or imino group. Aminations of azines are usually carried out by heating a π-deficient heterocycle with the metal salt of the conjugated base of an amine or amine in an inert, apolar solvent. Chichibabin amination is the first amino-dehydrogenation reaction. The treatment of pyridine with sodium amide in an inert aprotic solvent at elevated temperatures yields 2-aminopyridine in reasonable yield. The oxidative amination procedure is simple but varies depending on the structure of the substrate. The oxidative amino-dehydrogenation of monoazines, quinolines, naphthyridines, diazines, quinazolines, quinoxalines, triazines, tetrazines, and their bicyclic analogs is discussed in the chapter. Amination under homogeneous conditions is an important breakthrough in oxidative amination–dehydrogenation procedures. After addition of the amide ion to the azine, an anionic σ-adduct is formed, which is quite stable in the polar medium as shown by nuclear magnetic resonance (NMR) spectroscopy.
    Vicarious nucleophilic substitution of hydrogen vs. ANRORC-type ring transformation in reactions of 1,2,4-triazines with alpha-halocarbanions. Novel route to functionalized pyrazoles
    Rykowski, A. ; Wolinska, E. ; Branowska, D. ; Plas, H.C. van der - \ 2004
    ARKIVOC 2004 (2004)3. - ISSN 1551-7004 - p. 74 - 84.
    organic-anions - nitroarenes - sulfones
    A novel route to pyrazole derivatives bearing sulfonyl, aminosulfonyl, alkoxy- and aryloxysulfonyl groups at C-3 by ring transformation of 3-chloro-6-aryl-1,2,4-triazines 1a-c with alpha-halocarbanions 2a-h is described.
    Pyrimidine-pyridine ring interconversion
    Plas, H.C. van der - \ 2003
    Advances in Heterocyclic Chemistry 84 (2003)Suppl.. - ISSN 0065-2725 - p. 31 - 70.
    diels-alder reactions - heterocyclic halogeno compounds - nitrogen bridgehead compounds - active methylene reagents - one-step synthesis - potassium-amide - liquid-ammonia - transformation reactions - intramolecular cycloaddition - 6-substituted derivatives
    This chapter discusses the pyrimidine-to-pyridine ring transformation and pyridine-to-pyrimidine ring transformation. In nucleophile-induced pyrimidine-to-pyridine rearrangements, two types of reactions can be distinguished depending on the structure of the nucleophile: (1) reactions in which the nitrogen in the pyridine ring originates from the nitrogen of the pyrimidine ring or (2) reactions in which the pyridine nitrogen is derived from a nitrogen-containing reagent. In addition to nucleophile-induced transformations, the hetero Diels–Alder (HDA) cycloaddition reactions are also very suitable ways to perform the pyrimidine-to-pyridine ring transformations. To investigate the influence of substituents on the scope of the pyridine-to-pyrimidine ring transformation, a large number of 6-R-2-bromopyridines were investigated in an experiment. It was found that the ring transformation only occurs in quite limited cases. Only the 2-bromo-6-Ph-, 6-OPh- and 6-(substituted-C6H4O)-pyridines could be converted into the corresponding pyrimidine derivatives in reasonable yields (40–50%).
    Covalent nitromethylation of 2-, 3- and 4-nitroquinolines.
    Grzegozek, M. ; Wozniak, M. ; Plas, H.C. van der - \ 1994
    Polish Journal of Chemistry 68 (1994). - ISSN 0137-5083 - p. 635 - 638.
    Rede ter gelegenheid van de opening van het academisch jaar 1993/1994. Voordracht bij het afscheid als Rector Magnificus van de Landbouwuniversiteit
    Lubbers, R.F.M. ; Plas, H.C. van der - \ 1993
    Wageningen : Landbouwuniversiteit Wageningen - 16
    landbouw - beleid - colleges (hoorcolleges) - universiteiten - nederland - agriculture - policy - lectures - universities - netherlands
    Amination of nitroazaaromatics.
    Wozniak, M. ; Plas, H.C. van der - \ 1993
    Acta chemica scandinavica 47 (1993). - ISSN 0904-213X - p. 95 - 101.
    Conformations of some substituted porphyrins.
    Sanders, G.M. ; Dijk, M. van; Plas, H.C. van der - \ 1992
    Trends Organic Chemistry 3 (1992). - p. 261 - 277.
    Haloperoxidases, their use in organic synthesis.
    Franssen, M.C.R. ; Plas, H.C. van der - \ 1992
    In: Abstract 5th Meeting Bioorganic chemistry, Liblice Castle, Tsjechoslowakije - p. 26 - 27.
    Haloperoxidases: their properties and their use in organic synthesis.
    Franssen, M.C.R. ; Plas, H.C. van der - \ 1992
    In: Advances in applied microbiology, vol.37 / Neidleman, S.L., Laskin, A.I., San Diego : Academic Press Inc. - p. 41 - 99.
    Intramolecular Diels-Alder reactions of pyrimidines and a computational study toward their structure and reactivity.
    Stolle, W.A.W. ; Frissen, A.E. ; Marcelis, A.T.M. ; Plas, H.C. van der - \ 1992
    Journal of Organic Chemistry 57 (1992). - ISSN 0022-3263 - p. 3000 - 3007.
    Synthesis of molybdenum (V) and molybdenum (VI) derivatives of 5,15-diphenyl-2,8,12,18-tetra-n-butyl-3,7,13,17-tetramethylporphyrin.
    Dijk, M. van; Morita, Y. ; Petrovic, S. ; Sanders, G.M. ; Plas, H.C. van der; Stam, C.H. ; Wang, Y. - \ 1992
    Journal of heterocyclic chemistry 29 (1992). - ISSN 0022-152X - p. 81 - 86.
    Synthesis of 5-propynyloxycycloalkanepyrimidines and their selectivity and reactivity in intramolecular Diels-Alder reactions.
    Stolle, W.A.W. ; Veurink, J.M. ; Marcelis, A.T.M. ; Plas, H.C. van der - \ 1992
    Tetrahedron 48 (1992). - ISSN 0040-4020 - p. 1643 - 1656.
    Computational studies towards the selectivity and reactivity of 5-propynyloxycycloalkanepyrimidines in intramolecular Diels-Alder reactions.
    Stolle, W.A. ; Marcelis, A.T.M. ; Plas, H.C. van der - \ 1992
    Tetrahedron 48 (1992). - ISSN 0040-4020 - p. 1657 - 1666.
    Diels-Alder reactions of diazines and pyridines.
    Marcelis, A.T.M. ; Plas, H.C. van der - \ 1991
    Trends in Heterocyclic Chemistry 1 (1991). - p. 111 - 123.
    On the bipyridyl formation in reactions of 2-chloropyridine derivates with potassium amide in liquid ammonia.
    Streef, J.W. ; Plas, H.C. van der; Harkema, S. - \ 1991
    Collection of Czechoslovak Chemical Communications 56 (1991). - ISSN 0010-0765 - p. 2313 - 2325.
    Regioselectivity in SNH reactions of some 3-nitro-1,8-naphthyridines with chloromethyl phenyl sulfone.
    Grzegozek, M. ; Wozniak, M. ; Baranski, A. ; Plas, H.C. van der - \ 1991
    Journal of heterocyclic chemistry 28 (1991). - ISSN 0022-152X - p. 1075 - 1077.
    Quantitative structure-activity relationship (QSAR) studies of the inhibition of xanthine oxidase by heterocyclic compounds.
    Naeff, H.S.D. ; Franssen, M.C.R. ; Plas, H.C. van der - \ 1991
    Recueil des travaux chimiques des Pays-Bas = Journal of the Royal Netherlands Chemical Society 110 (1991). - ISSN 0165-0513 - p. 139 - 150.
    Reactivity of 2-pent-4-yn-1-ylpyrimidines in intramolecular Diels-Alder reactions. Molecular mechanics and MNDO calculations and crystal structure determinations.
    Stolle, W.A.W. ; Frissen, A.E. ; Marcelis, A.T.M. ; Plas, H.C. van der; Wang, Y. ; Häming, L. ; Stam, C.H. - \ 1991
    Journal of Organic Chemistry 56 (1991). - ISSN 0022-3263 - p. 2411 - 2416.
    A computational study towards the reactivity of 2-(2-ethynylphenyl-x-)pyrimidines in intramolecular Diels-Alder reactions.
    Stolle, W.A.W. ; Marcelis, A.T.M. ; Plas, H.C. van der - \ 1991
    Tetrahedron 47 (1991). - ISSN 0040-4020 - p. 1753 - 1764.
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