AbstractThe novel "unsymmetric" title compounds (III) are prepared by Claisen condensation of the pyridinecarboxylates (I) with the acetylpyridines (II).

AbstractBis‐arylethenylpyridine N‐oxides such as (III) or (V) are prepared from the dimethylpyridine N‐oxide (I); the "mono" product (VI) is additionally formed in the latter case.

ChemInformVolume 20, Issue 33 Preparative Organic Chemistry ChemInform Abstract: Mannich and Grignard Reaction of Some N-(2-Propynyl) Azaheterocycles. A. SILHANKOVA, A. SILHANKOVA Dep. Org. Chem., Prague Inst. Chem. Technol., 166 28 Prague 6Search for more papers by this authorM. HOSKOVEC, M. HOSKOVEC Dep. Org. Chem., Prague Inst. Chem. Technol., 166 28 Prague 6Search for more papers by this authorR. LIBOSKA, R. LIBOSKA Dep. Org. Chem., Prague Inst. Chem. Technol., 166 28 Prague 6Search for more papers by this authorM. FERLES, M. FERLES Dep. Org. Chem., Prague Inst. Chem. Technol., 166 28 Prague 6Search for more papers by this author A. SILHANKOVA, A. SILHANKOVA Dep. Org. Chem., Prague Inst. Chem. Technol., 166 28 Prague 6Search for more papers by this authorM. HOSKOVEC, M. HOSKOVEC Dep. Org. Chem., Prague Inst. Chem. Technol., 166 28 Prague 6Search for more papers by this authorR. LIBOSKA, R. LIBOSKA Dep. Org. Chem., Prague Inst. Chem. Technol., 166 28 Prague 6Search for more papers by this authorM. FERLES, M. FERLES Dep. Org. Chem., Prague Inst. Chem. Technol., 166 28 Prague 6Search for more papers by this author First published: August 15, 1989 https://doi.org/10.1002/chin.198933110Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume20, Issue33August 15, 1989 RelatedInformation

1,4-Disubstituted butynes IV-VII were prepared by Mannich reaction of N-(2-propynyl) derivatives of 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline, piperidine and azacycloheptane with polyoxymethylene and another heterocyclic amines. Reaction of 3-(1-piperidinyl)-1-propynylmagnesium bromide or 3-(1-azacycloheptyl)-1-propynylmagnesium bromide afforded alcohols X-XIII.

Preparation d'oxydes-1 d'aryl- et d'heterylvinyl pyridines par condensation des oxydes-1 des dimethyl-2,4 (−2,6) pyridines avec des aldehydes aromatiques et heteroaromatiques catalysee par le t-butanolate de potassium. Etude de la condensation des dimethylpyridines avec le pyridinecarbaldehyde-3 et des oxydes-1 des dimethylpyridines avec l'oxalate de diethyle

Photochemical addition of methanol to 1,2,3,6-tetrahydropyridine derivatives Ia, Ib, Id-Ii and III afforded methoxypiperidines IIa-IIg and IV as Markovnikov type addition products. Reduction of 4-methyl-1-(2-propenyl)pyridinium bromide with sodium borohydride yielded 4-methyl-1-(2-propenyl)-1,2,3,6-tetrahydropyridine (Ig).

AbstractThe title compounds (I) and (V) are hydroborated by four methods: THF‐borane (method A)), 9‐borabicyclononane (method C)), diborane in situ (method D)) and NEt3‐borane (method E)).

1-(5-Hexenyl)piperidine (Ia) and trans-1-(3-hexenyl)piperidine (Ib) were hydroborated with tetrahydrofuran-borane, diborane in situ, 9-borabicyclo[3.3.1]nonane and triethylamine-borane. The hydroboration products were converted to 1-piperidinylhexanols IIa-IIe by hydrolysis with hydrochloric acid and subsequent oxidation with hydrogen peroxide in an alkaline medium. In addition to the alcohols IIa-IIe, the reaction also gave 1-hexylpiperidine (Ic). In the reactions with diborane in situ and triethylamine-borane, thermal isomerization of the hydroboration products was also studied. Hydroboration of Ia with triethylamine-borane afforded a mixture of spirocyclic amine-boranes IIIa-IIIc from which 6-(1-piperidinyl)-3-hexylboronic acid hydrochloride (IV) was obtained by hydrolysis with hydrochloric acid. Compounds IIIa-IIIc were slowly decomposed with ethanol to give esters of boronic acids Id-If. The synthesis of compounds Ia and Ib is described.

AbstractThe title compound (I) is hydroborated with NEt3‐borane, diborane in situ, THF‐borane and 9‐borabicyclononane (9‐BBN).

Hydroboration of N,N-dimethyl(2-vinylbenzyl)amine followed by oxidation afforded a mixture of primary and secondary alcohol, i.e. 2-(2-dimethylaminomethylphenyl)ethanol and 1-(2-dimethylaminomethylphenyl)ethanol, together with the reduction product – 2-ethyl(N,N-dimethylbenzylamine).

AbstractDas Tetrahydrochinolin (III) wird thermisch zu dem Tetrahydrobenzochinolizin (IVa) cyclisiert, von dem die Derivate (IVb)‐(IVd) abgeleitet werden.

Hydroboration of 1-allyl-1,2,3,4-tetrahydroquinoline (I) with triethylamine-borane in the molar ratio 1 : 1 afforded a product from which 6,7-benzo-5-aza-1-boraspiro[4,5]decane (II) was isolated. Ethanolysis of II gave diethyl 3-(1,2,3,4-tetrahydro-1-quinolyl)propylboronate (III). Acid hydrolysis of the crude hydroboration product and subsequent oxidation with alkaline hydrogen peroxide led to a mixture of 3-(1,2,3,4-tetrahydro-1-quinolyl)-1-propanol (IV), 1,2,3,4-tetrahydroquinoline (V) and 1-propyl-1,2,3,4-tetrahydroquinoline (VI). Hydroboration of I with triethylamine-borane in the molar ratio 3 : 1, followed by oxidation, gave a mixture of IV, V, VI and 1-(1,2,3,4-tetrahydro-1-quinolyl)-2-propanol (VIII). Hydroboration of I with diborane in situ in diethylene glycol dimethyl ether at 20 °C and subsequent acid hydrolysis and oxidation with alkaline hydrogen peroxide afforded a mixture of IV, V and VIII when the hydroboration product was first heated to 150 °C and then subjected to the above-mentioned processing, only compounds IVand V were formed.

Reaction of 1,2,3,4-tetrahydroquinoline with 1-chloro-2,3-epoxypropane afforded l-(3-chloro-2-hydroxypropyl)-l,2,3,4-tetrahydroquinoline (IIb) which was thermolabile and on heating in vacuo was converted into 2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-2-ol (Ib). This compound reacted with acetic anhydride and p-toluenesulfonyl chloride to give 2-acetoxy-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine (Ic) and 2-(p-toluenesulfonyloxy)-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine (Id), respectively. N,N-Bis(3-chloro-2-hydroxypropyl)aniline (IIIb) on heating gave a mixture of cis- and trans-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine-2,6-diols (Ie). The corresponding 4-methoxyaniline derivative afforded analogously a mixture of cis- and trans-9-methoxy-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine-2,6-diols (If). Dehydration with potassium hydroxide converted the diols Ie into 1H,7H-benzo[ij]quinolizine (VIa), the diols If into 9-methoxy-1H,7H-benzo[ij]quinolizine (VIb). Treatment of Ib with phosphorus pentoxide led to 2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine (julolidine, Ia).

Bei der Hydroborierung von (II) mit l Äquiv.