Antikonvulsiva, 1. Mitt. Thiocarbamoylbutyroguanamine

Kreutzberger, A.; Loch, M.

doi:10.1002/ardp.19863190902

Cited by 3 publications

(1 citation statement)

References 3 publications

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“…The tertbutyl groups are disordered. Similar intramolecular hydrogen bonds have already been found in 2-pyridylthioureas, triazinylureas, and -thioureas by either 1 H NMR spectroscopy or X-ray crystallography [54][55][56][57]. The spectral properties of azacyclic thioureas 5 in CDCl 3 differ from those of Takemoto's catalyst 3, NH signals of which are not visible at ambient temperature in the same solvent due to chemical exchange, but can be resolved at low temperature, where the presence of two monomeric conformers and two dimeric associates is revealed [58].…”

Section: Resultsmentioning

confidence: 66%

2-Amino-1,3,5-triazine chemistry: hydrogen-bond networks, Takemoto thiourea catalyst analogs, and olfactory mapping of a sweet-smelling triazine

2015

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The chemistry of 4,6-dialkyl-2-amino-1,3,5-triazines with bulky alkyl substituents was investigated and their use as building blocks for preparing chiral thiourea organocatalysts explored. Reaction of ammonia with 4,6-di-tert-butyl-2-chloro-1,3,5-triazine gave 4,6-di-tert-butyl-1,3,5-triazin-2-amine which formed extended hydrogenbond networks in the solid state according to X-ray crystallography. Selected heterocyclic amines were converted to isothiocyanates, and the latter reacted with (S,S)-2-(dimethylamino)cyclohexylamine to give enantiopure 1-hetaryl-3-[2-(dimethylamino)cyclohexyl]thioureas, with hetaryl representing either 4,6-dimethyl-1,3-diazin-2-yl, 4,6-diisopropyl-1,3,5-triazin-2-yl, or 4,6-di-tert-butyl-1,3, 5-triazin-2-yl groups. These compounds are structural analogs of Takemotos's chiral thiourea organocatalysts (1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1S,2S)-2-(dimethylamino)cyclohexyl]thiourea) with an aza-aryl instead of the 3,5-bis(trifluoromethyl)phenyl group. They feature a strong intramolecular N-H to N-1 hydrogen bond, as shown by X-ray crystallography of 1-(4,6-di-tert-butyl-1,3,5-triazin-2-yl)-3-[2-(dimethylamino)cyclohexyl]thiourea in the solid state and by 1 H NMR spectroscopy of all derivatives in CDCl 3 solution, which prevents them from acting as bifunctional organocatalyst. In the reaction of 4,6-di-tertbutyl-2-chloro-1,3,5-triazine with ammonia, 4,6-di-tertbutyl-2-ethoxy-1,3,5-triazine was identified as side-product displaying a mildly sweet, floral odor that is unusual for a 1,3,5-triazine. Analogs ([35) of 4,6-di-tert-butyl-2-ethoxy-1,3,5-triazine were prepared to define the important structural factors of the olfactophore. Graphical abstract N N N H N tBu tBu N S H Me 2 N N N N NH 2 tBu tBu

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Section: Resultsmentioning

confidence: 66%

2-Amino-1,3,5-triazine chemistry: hydrogen-bond networks, Takemoto thiourea catalyst analogs, and olfactory mapping of a sweet-smelling triazine

2015

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Trichomonazide Wirkstoffe, 3. Mitt. Aryloxy‐chlor‐1,3,5‐triazine

Kreutzberger

Rose

1987

Archiv der Pharmazie

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Die Umsetzung von 2,4-Dichlor-6-(dihexylamino)-1,3,5-triazin (1) mit Phenolen (2) fiihrt bei niedrigen Temperaturen zu den Monoaryloxy-chlor-1,3,5-triazinen (3a-c), unter drastischeren Reaktionsbedingungen zu den Bis-(aryloxy)-1,3,5-triazinen (4c-d). Fur die neuen Verbindungstypen ist besonders charakteristisch die rnassenspektroskopische Abspaltung der Aryloxygruppen, beispielsweise in 4c der Ubergang von m/z 504 nach m/z 383. Auffallende trichomonazide und blutzuckersenkende Wirkungen vermag insbesondere 3b auszulosen.

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