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Beta-Enaminoamides and synthesis of six-membered heterocyclic compounds containing boron atom
Authors: Svobodová Markéta | Bárta Jan | Šimůnek Petr | Bertolasi Valerio | Macháček Vladimír
Year: 2007
Type of publication: ostatní - přednáška nebo poster
Name of source: 15th European Symposium on Organic Chemistry
Publisher name: University College Dublin
Page from-to: nestránkováno
Titles:
Language Name Abstract Keywords
cze Beta-Enaminoamidy a syntéza šestičlenných heterocyklických sloučenin obsahujících atom boru β-Enaminony typu I byly podrobeny reakci se 4-subst.benzendiazonium-tetrafenylboráty. Produkty těchto reakcí byly tetrasubstituované či pentasubstituované heterocyklické sloučeniny. Jestliže byly oxazaboriny II zahřáty buď ve vroucím toluenu nebo bez rozpouštědla (200 °C), došlo k jejich přesmyku na triazaboriny III, a to v 52?84% výtěžku. Reakcí β-enaminoamidů IV majících primární aminoskupinu (R2 = H) se 4-methylbenzendiazonium-tetrafenylborátem vzniká směs produktů, které byly identifikovány jako oxazaborin V, diazaborinon VI a triazaborin VII (Schéma 2). Reakce probíhá v dichlormethanu při laboratorní teplotě. Jestliže R2 = Me, byly získány pouze oxazaborin a triazaborin. Enaminoamidy, diazonium-tetrafenylboráty, heterocykly, oxazaboriny, diazaborinony, triazaboriny, NMR, X-ray,
eng Beta-Enaminoamides and synthesis of six-membered heterocyclic compounds containing boron atom β-Enaminones I were subjected to the reaction with 4-subst.benzenediazonium tetraphenylborates to give tetrasubstituted or pentasubstituted heterocyclic compounds II. When the oxazaborines II were heated in boiling toluene or without the solvent (200 °C) a recyclization occurred to give new triazaborines III in 52?84% yield. The reaction of β-enaminoamides IV having the primary amino group (R2 = H) with 4 methylbenzenediazonium tetraphenylborate gives the mixture of products, which were identified as oxazaborine V, diazaborinone VI and triazaborine VII (Scheme 2). This reaction was carried out in dichloromethane at laboratory temperature. The reaction time was about fourtimes longer than in the case of the reaction of β-enaminones I. Oxazaborines and triazaborines were obtained when R2 was a methyl group. Enaminoamides, diazonium tetraphenylborates, heterocycles, oxazaborines, diazaborinones, triazaborines, NMR, X-ray

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