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2 article(s) from Decker, Michael

Experimental and theoretical investigations into the stability of cyclic aminals

Edgar Sawatzky,
Antonios Drakopoulos,
Martin Rölz,
Christoph Sotriffer,
Bernd Engels and
Michael Decker

Beilstein J. Org. Chem. 2016, 12, 2280–2292, doi:10.3762/bjoc.12.221

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Figure 1: Compounds described in the literature containing an aminal core for various applications. The amina...

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Scheme 1: Synthetic approaches for the formation of the tetrahydroquinazoline moiety. Dashed lines indicate b...

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Scheme 2: Oxidation and reduction reactions of tetrahydroquinazolines. Dashed lines indicate both cyclized or...

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Figure 2: Hydrolysis of the aminal core of tetrahydroquinazolines 1 into the corresponding diamines 2 and ald...

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Scheme 3: Reagents and conditions: (i) MeI, DIPEA, DMAc, 40 °C, 24 h; (ii) R¹-NH₂ or MeNH₃Cl and Et₃N, DMF, 4...

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Scheme 4: Reagents and conditions: (a) (i) MeNH₃Cl, Et₃N, DMF, 70 °C, 3 h; (ii) AcOH, 70 °C, 4 h; (iii) n-PrB...

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Figure 3: pH-Stability test of the aminal core toward hydrolysis in dependency of different substitution patt...

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Figure 4: Kinetic analysis of hydrolysis of reference compound 8a in dependency of different pH values and ca...

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Figure 5: Differences in energy along the reaction coordinate using the functional B3LYP-D3 for the hydrolysi...

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Figure 6: Reaction equilibrium between tetrahydroquinazoline 1, the corresponding diamine 2 and aldehyde 3 in...

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Figure 7: Minimum energy conformers in their neutral form with (a) an axial orientation of the phenyl system ...

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Full Research Paper

Published 31 Oct 2016

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Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

Guozheng Huang,
Simon Schramm,
Jörg Heilmann,
David Biedermann,
Vladimír Křen and
Michael Decker

Beilstein J. Org. Chem. 2016, 12, 662–669, doi:10.3762/bjoc.12.66

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Figure 1: Structures of silibinin, isosilybin, and silychristin, and hydnocarpin-type flavonolignans.

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Figure 2: Synthetic strategy of semi-synthesis of hydnocarpins from silybins [22].

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Scheme 1: Synthesis of ester derivatives of silibinin and conversion to hydnocarpin-type compounds. Reaction ...

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Figure 3: Putative mechanism of dehydration of flavanonols under Mitsunobu conditions.

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Scheme 2: Attempt to dehydrate catechin. Reagents and conditions: a) p-nitrobenzoic acid, Ph₃P, DIAD, THF, rt...

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Scheme 3: Preparation of hydnocarpin (4) and isohydnocarpin (6) and attempt to dehydrate silydianin A (11). R...

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Published 08 Apr 2016

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