Nucleophile Substitution des Pyridins

Dobeneck, Henning Von; Deubel, Heinz; Heichele, F.

doi:10.1002/ange.19590710906

Cited by 10 publications

(2 citation statements)

References 2 publications

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“…N-Acylpyridinium salts have also been condensed with indoles to yield either the 1,4-dihydroacylpyndyl derivative 111-300 (375) or the pyridinium salt III-301, the product obtained depending on the solvent and the reactant ratio reaction, it was found that, in general, aroylpyridinium salts gave higher yields than did the aliphatic derivatives, presumably because the aromatic substituents have the stronger electron-withdrawing power. The yields also were dependent on the nature of the anion, increasing in the order Cl, Br, I, and on the length of the aliphatic acyl chain (377).…”

Section: -298 111299mentioning

confidence: 99%

Quaternary Pyridinium Compounds

Rodig¹

1974

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Section: -298 111299mentioning

confidence: 99%

Quaternary Pyridinium Compounds

Rodig¹

1974

Chemistry of Heterocyclic Compounds: A Series of Monographs

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“…Schon wahrend der Reduktion beginnt die Tetrahvdropyridinbase auszukristalli-Tabelle 2 ") . Pyridiniumsalxe, ( I ,2,3, [4].…”

Section: -(4-pyridyl)-indol (11) -Eine Mischung Von 60 G L-benzoyl-unclassified

Synthese von 2‐ und 3‐(1,2,3,6‐Tetrahydropyridyl)‐indolen

Beck¹,

Schenker²

1968

Helvetica Chimica Acta

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Oxazolidindion‐Derivate und 4‐[Piperidyl‐(4′)]‐antipyrine als potentiell entzündungshemmende Substanzen

Schulte

Weissenborn

Loesevitz

1980

Archiv der Pharmazie

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Oxazolidindion-und Antipyrn-Derivate 229 ausgeschuttelt. Nach Trocknen uber Na2SO4 und Entfernung des Et,O erhalt man die gewunschte Substanz. Gelbliches 0 1 , Ausb.: 10 % d. Th. -270-MHz-IH-NMR-(CDCI,): 6 (ppm) = 7.5-7.0 (m, 5H, aromat.), 2.41 (s, 6H, N(CH,),), 2.00 (ddd, J = 9/6/3 Hz, lH, HA, siehe Text), 1.82 (ddd, J = 7.514.513 Hz, lH, HM), 1.11 (ddd, J = 9/5/4.5 Hz, lH, HR), 0.95 (ddd, J = 7.5/6/5 Hz, l H , HX). Von 5-disubstituierten 2,4-Oxazolidindionen lassen sich dann N-Acyl-Derivate (1, R3 = Arylsulfonyl bzw. Aroyl-) mit guter Ausbeute und ohne Nebenprodukte (Diarylsulfone bzw. Aroylanhydride) darstellen, wenn die Umsetzung mit den Acylchloriden in Gegenwart aquivalenter Mengen Aluminiumchlorid in Pyridin/ Acetonitril(1 : 1) erfolgt. Auch 5-Methyl-2,4-oxazolidindion laBt sich unter diesen Reaktionsbedingungen acylieren, nicht dagegen das 5-Phenyl-2,4-oxazolidindion. Bei **) Teil der Dissertation B. Loesevitz, Miinster 1977. 03654233/80/0303-4229 $02.50/0 8 Verlag Chemie, GmbH, Weinheim 1980 230 Schulte, v. Weissenborn und Loesevitz Arch. Pharm. letzterer Verbindung tritt Pyridylierung am C-5 ein; es entsteht 4. Eine Pyridylierung geht Antipyrin bei Abwesenheit von AICI, ein, wenn als weiterer Reaktionspartner Chlorameisensaureester eingesetzt wird; es entsteht 6, aus dem durch Hydrierung 4-(Piperidyl-(4')]-antipyrine zu gewinnen sind. Oxazolidinedione Derivatives and 4-(4-Piperidyl)phenazones as Potential Anti-inflammatory AgentsN-Acyl derivatives (1, R3 = arylsulfonyl or aroyl) can be prepared by treating 5,5-disubstituted 2,4-oxazolidinediones with acyl chlorides in the presence of equivalent amounts of aluminium chloride in pyridine/acetonitrile (1 : 1). Yields are high and there are no by-products (diarylsulphonesor aroyl anhydrides). 5-Methyl-2,4-oxazolidinedione, but not 5-phenyl-2,4-oxazolidinedione, can be acylated under these conditions. 5-Phenyl-2,4-oxazolidinedione is pyridylated at C-5 to give 4. Phenazone can be pyridylated in the absence of AICI, but in the presence of chloroformates to give compounds 6, which can be reduced to give 4-(4piperidyl)phenazones.

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Nucleophile Substitution des Pyridins

Cited by 10 publications

References 2 publications

Quaternary Pyridinium Compounds

Quaternary Pyridinium Compounds

Synthese von 2‐ und 3‐(1,2,3,6‐Tetrahydropyridyl)‐indolen

Oxazolidindion‐Derivate und 4‐[Piperidyl‐(4′)]‐antipyrine als potentiell entzündungshemmende Substanzen

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