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2 article(s) from Hommes, Paul

Synthesis of highly functionalized 2,2'-bipyridines by cyclocondensation of β-ketoenamides – scope and limitations

Paul Hommes and
Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2016, 12, 1170–1177, doi:10.3762/bjoc.12.112

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Scheme 1: Synthesis of highly functionalized 2,2'-bipyridines 4a and 5b from symmetrical 1,3-diketones 1a and ...

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Scheme 2: Synthesis of β-ketoenamines 2c–e and of β-ketoenamides 3c–h.

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Scheme 3: Synthesis of α-methoxy-β-ketoenamine 2i, its N-acylation to 3i and the reaction of β-ketoenamide 3a...

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Scheme 4: Cyclizations of β-ketoenamide 3i leading to 2,2´-bipyridine derivative 4i or to the related 2-(2-py...

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Scheme 5: Suzuki-couplings of 2,2'-bipyrid-4-yl nonaflates 5a and 5b to compounds 9 and 10.

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Scheme 6: Palladium-catalyzed couplings of chloro-substituted 2,2'-bipyrid-4-yl nonaflate 5g leading to compo...

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Published 09 Jun 2016

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The Flögel-three-component reaction with dicarboxylic acids – an approach to bis(β-alkoxy-β-ketoenamides) for the synthesis of complex pyridine and pyrimidine derivatives

Mrinal K. Bera,
Moisés Domínguez,
Paul Hommes and
Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 394–404, doi:10.3762/bjoc.10.37

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Scheme 1: Flögel-three-component reaction of lithiated alkoxyallenes, nitriles and carboxylic acids providing...

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Scheme 2: Synthesis of bis(β-ketoenamides) 13–15 by three-component reactions of lithiated methoxyallene 8 wi...

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Scheme 3: Cyclocondensations of β-ketoenamides 13 and 14 to 4-hydroxypyridines 16, 18a and 18b, their subsequ...

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Scheme 4: Cyclocondensations of β-ketoenamides 13–15 with ammonium acetate to bis(pyrimidine) derivatives 23a...

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Scheme 5: Conversion of mono-pyrimidine derivative 24b into unsymmetrically substituted biphenylen-bridged py...

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Scheme 6: Condensation of β-ketoenamides 14 and 20 with hydroxylamine hydrochloride to pyridine-N-oxides 28 a...

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Scheme 7: Riley oxidation of bis(pyrimidine) derivative 23a and conversion of diol 32a into macrocycle 34.

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Figure 1: Optimized geometries of (a) E-configured and (b) Z-configured macrocycle 34 at B3LYP/6-31G(d,p) lev...

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Scheme 8: Dihydroxylation of the macrocyclic olefin 34 to diol 35 and subsequent esterification to the bis-(R...

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Published 13 Feb 2014

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