- Process for preparing cyano derivatives of tetrahydroquinolines and related compounds
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Fused carbocyclic ring derivatives of pyridine which contain a nitrile or thioamide group on the carbocyclic ring e.g. 8-cyano or thiocarboxamido-5,6,7,8-tetrahydroquinolines are prepared by a process in which a sodium, potassium, lithium or magnesium halide derivative of the pyridine compound is treated with a compound RaRbNCN wherein Ra and Rb are the same or different and represent alkyl, cycloalkyl, or aralkyl, or Ra and Rb are joined to form a heterocyclic ring with the nitrogen, and the product is treated with a proton source to obtain the nitrile which is optionally treated with a sulphurizing agent to form the thioamide. The nitriles or thioamides may be isolated as their acid addition salts.
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- 5,6,7,8-Tetrahydroquinolines. Part 7. Synthesis of 8-Cyano-5,6,7,8-tetrahydroquinolines; Di-isopropylcyanamide, a New Reagent for Cyanation of Organometallics
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Di-isopropylcyanamide (1) is an effective reagent for the conversion of 8-lithio-5,6,7,8-tetrahydroquinolines into 8-cyano-5,6,7,8-tetrahydroquinolines. 8,8-Dicyano derivatives are not formed.A convenient synthesis of the reagent from disodium cyanamide is described.
- Crossley, Roger,Shepherd, Robin G.
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p. 2479 - 2482
(2007/10/02)
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- Certain 5,6,7,8-tetrahydroquinoline-8-thiocarboxamides
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The invention relates to novel pyridine derivatives which have a fused 5,6, or 7-membered saturated hydrocarbon ring adjacent to the nitrogen of the pyridine ring, and a group X situated on said hydrocarbon ring and separated by one carbon atom from the pyridine nitrogen atom, said group X is cyano, CONHR3, CSNHR3 or CO2 R5 wherein R3 is selected from hydrogen, lower alkyl and lower aralkyl radicals and R5 is selected from hydrogen, lower alkyl and lower aralkyl radicals which may be substituted by alkyl, alkoxy, halogen, nitro or trifluoromethyl; other substituents may be present. Compounds wherein X is CSNHR3 are anti-ulcer agents and the other compounds are intermediates therefor.
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- 8-Carboxylester, and 8-carbamyl derivitives of 5,6,7,8-tetrahydroquinoline
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The invention relates to novel 5,6,7,8-tetrahydroquinoline derivatives which have a group X situated at the 8-position said group X is CONHR3, or CO2 R5 wherein R3 is hydrogen lower alkyl and R5 is hydrogen, lower alkyl or a lower aralkyl radical. The compounds are intermediates for corresponding compounds where X is CSNHR3 and these are anti-ulcer agents.
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- Cyclopenteno[b]pyridine derivatives
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The invention relates to novel cyclopenteno[b]pyridine derivatives which have a thioamide group in the 7-position and related tricyclic compounds. The compounds are anti-ulcer agents.
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- 8-Cyano-5,6,7,8-tetrahydroquinoline derivatives
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The invention relates to novel 8-cyano-5,6,7,8-tetrahydroquinoline derivatives which are intermediates for the preparation of corresponding 8-thioamides. Some of the 8-cyano compounds are anti-ulcer agents.
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- Cyclopenteno[b]pyridine derivatives
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The invention relates to novel cyclopenteno[b]pyridine derivatives which have a group X on the 7-position and related tricyclic compounds. X is CONHR3, or CO2 R5 wherein R3 is hydrogen or lower alkyl and R5 is hydrogen or a lower alkyl or lower aralkyl group which may be substituted by alkyl, alkoxy, halogen, nitro or trifluoromethyl; other substituents may be present. The compounds are intermediates for compounds wherein X is CSNHR3 which are anti-ulcer agents.
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- Pharmaceutical compositions containing 5,6,7,8-tetrahydroquinoline derivatives and related compounds
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The invention relates to pharmaceutical compositions containing 5,6,7,8-tetrahydroquinoline-8-thioamides and nitriles and related tricyclic compounds and methods of treating ulcers using said compounds.
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