AT266137B - Process for the production of new pyridyl-dihydroisoquinolines and their salts - Google Patents
Process for the production of new pyridyl-dihydroisoquinolines and their saltsInfo
- Publication number
- AT266137B AT266137B AT1044767A AT1044767A AT266137B AT 266137 B AT266137 B AT 266137B AT 1044767 A AT1044767 A AT 1044767A AT 1044767 A AT1044767 A AT 1044767A AT 266137 B AT266137 B AT 266137B
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- Austria
- Prior art keywords
- lower alkyl
- carbon atoms
- salts
- radical
- hydrogen atom
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung neuer Pyridyl-dihydroisochinoline sowie von deren
Salzen
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von neuen Pyridyl-dihydroisochinolinen der allgemeinen Formel :
EMI1.1
EMI1.2
Formel haben die Reste Ri-Rg folgende Bedeutung : Ri ist ein niederer Alkylrest bis zu 5 Kohlenstoffatomen, ein gegebenenfalls durch eine Methylgruppe oder ein Halogenatom substituierter Benzylrest, R ist ein niederer Alkylrest bis zu 5 Kohlenstoffatomen ; Ri und Ru können auch zusammen mit dem benachbarten Kohlenstoffatom einen Cycloalkanring mit
5 oder 6 Kohlenstoffatomen bedeuten ; R3 ist ein Wasserstoffatom, ein niederer Alkylrest oder ein Halogenatom ; R und Rg sind Wasserstoffatome und/oder niedere Alkylreste.
Gemäss der Erfindung werden die Verbindungen der Formel I durch Cyclisierung unter Wasserabspaltung eines 3-oder 4-Pyridincarbonsäureamids der allgemeinen Formel :
EMI1.3
in der RI, R2, Rs, R4 und Rs die eingangs erwähnten Bedeutungen besitzen, erhalten.
Die Cyclisierung der 3-und 4-Pyridincarbonsäureamide der Formel II zu den entsprechenden Pyridyldihydroisochinolinen der Formel I erfolgt in der für Ringschlüsse nach Bischler-Napieralski üblichen Weise durch Behandeln mit den hiefür gebräuchlichen Cyclisierungsmitteln, beispielsweise Phosphoroxychlorid, Zinkchlorid, Phosphorpentachlorid und Polyphosphorsäureester als Cyclisierungsmittel. Besonders vorteilhaft ist die Verwendung von Phosphorpentoxyd oder einem Gemisch aus Phosphoroxychlorid mit Phosphorpentoxyd oder einer Mischung aus Phosphoroxychlorid und Zinkchlorid oder von Polyphosphorsäure.
In manchen Fällen ist es von Vorteil, wenn man das Pyridincarbonsäureamid zuerst mit Phosphorpentachlorid und dann mit Aluminiumchlorid behandelt.
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EMI2.1
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EMI3.1
pyridin-4-carbonsäureamid (F. = 148 C) die gewünschte Verbindung, deren Dihydrochlorid bei 236 C schmilzt.
EMI3.2
11 : 3, 4-Dihydro-3, 3-dimethyl-l- (4-methyl-3-pyridyl)-isochinolin.pyridin-3-carbonsäureamid (F. = 74-75 C) die gewünschte Verbindung, deren Dihydrochlorid bei 240 C schmilzt.
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Process for the production of new pyridyl-dihydroisoquinolines and their
Salt
The present invention relates to a process for the preparation of new pyridyl-dihydroisoquinolines of the general formula:
EMI1.1
EMI1.2
Formula, the radicals Ri-Rg have the following meaning: Ri is a lower alkyl radical up to 5 carbon atoms, a benzyl radical optionally substituted by a methyl group or a halogen atom, R is a lower alkyl radical up to 5 carbon atoms; Ri and Ru can also form a cycloalkane ring together with the adjacent carbon atom
Mean 5 or 6 carbon atoms; R3 is a hydrogen atom, a lower alkyl group or a halogen atom; R and Rg are hydrogen atoms and / or lower alkyl radicals.
According to the invention, the compounds of the formula I are obtained by cyclization with elimination of water of a 3- or 4-pyridinecarboxamide of the general formula:
EMI1.3
in which RI, R2, Rs, R4 and Rs have the meanings mentioned at the beginning.
The cyclization of the 3- and 4-pyridinecarboxamides of the formula II to the corresponding pyridyldihydroisoquinolines of the formula I is carried out in the manner customary for ring closures according to Bischler-Napieralski by treatment with the cyclizing agents customary for this purpose, for example phosphorus oxychloride, zinc chloride, phosphorus pentachloride and polyphosphoric acid esters as cyclizing agents. The use of phosphorus pentoxide or a mixture of phosphorus oxychloride with phosphorus pentoxide or a mixture of phosphorus oxychloride and zinc chloride or of polyphosphoric acid is particularly advantageous.
In some cases it is advantageous to treat the pyridinecarboxamide first with phosphorus pentachloride and then with aluminum chloride.
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EMI2.1
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EMI3.1
pyridine-4-carboxamide (m.p. = 148 C) the desired compound, the dihydrochloride of which melts at 236 C.
EMI3.2
11: 3, 4-dihydro-3, 3-dimethyl-l- (4-methyl-3-pyridyl) -isoquinoline.pyridine-3-carboxamide (M.p. = 74-75 C) the desired compound, the dihydrochloride of which at 240 C melts.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE266137X | 1965-12-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
AT266137B true AT266137B (en) | 1968-11-11 |
Family
ID=5997328
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AT1044767A AT266137B (en) | 1965-12-10 | 1966-03-22 | Process for the production of new pyridyl-dihydroisoquinolines and their salts |
Country Status (1)
Country | Link |
---|---|
AT (1) | AT266137B (en) |
-
1966
- 1966-03-22 AT AT1044767A patent/AT266137B/en active
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