53400-67-2Relevant academic research and scientific papers
Silyl compounds
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, (2008/06/13)
The invention provides new silyl derivatives of 5,6,7,8-tetrahydroquinolines and related compounds. The tetrahydroquinolines are substiuted at the 8-position by the group SiR3 where R may be one of various hydrocarbon groups or an electron donating substituent. The 8-position may also carry a lithium, sodium or potassium atom. The new silyl derivatives may be prepared by treating a corresponding 8-lithio, sodio or potassio tetrahydroquinoline with a silyl halide R3 SiHal followed by a metal compound R*M where M is sodium, potassium or lithium and R* is alkyl, cycloalkyl, aralkyl or aryl or an amine residue. The new silyl derivatives are useful intermediates for the preparation of known 5,6,7,8-tetrahydroquinline-8-nitriles, amides and thioamides employing an alkyl silyl isothiocyanate or cyanate. The nitriles and thioamides are anti-ulcer agents. The related compounds may be made by analogous methods.
5,6,7,8-Tetrahydroquinolines. Part 6. Silylation vs. Thioamidation in the Reaction of Silyl Isothiocyanates with Organometallics: Influence of the Solvent and of the Substituent on Silicon.
Crossley, Roger,Shepherd, Robin G.
, p. 1917 - 1920 (2007/10/02)
The influence of a number of variables on carbophilic vs. silicophilic attack by 8-lithio-3-methyl-5,6,7,8-tetrahydroquinoline on silyl isothiocyanates is reported.In general carbophilic attack (i.e. thiomidation) is favoured in solvents of low polarity a
Preparation of tetrahydroquinolines and related compounds
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, (2008/06/13)
An improved process for preparing tetrahydroquinolines and related compounds especially 5,6,7,8-tetrahydroquinoline-8-nitriles, amides and thioamides is described. The nitriles and thioamides are anti-ulcer and/or anti-secretory agents. Typically a compound of formula A STR1 where M is sodium, potassium, lithium or MgHal where Hal is chlorine, bromine or iodine, is reacted, e.g., in an ether solvent, with a silyl compound Rxa Si(NCY)4-x (III) wherein Ra is alkyl, cycloalkyl, aralkyl, or aryl, at least one group Ra being a branched chain alkyl, cycloalkyl, aryl or branched chain aralkyl, Y is oxygen or sulphur, x has a value from 1 to 3, then subjecting the product to hydrolysis or alcoholysis, to obtain the corresponding nitrile, amide or thioamide, provided that when a nitrile is desired the molar ratio of compound III to compound A is at least 2:1 and x is 3 and Y is S. The products may be obtained as acid addition salts. Compound A may contain various substituents, e.g., hydrocarbon substituents. Some compounds of formula III are novel and are also claimed.
Process for preparing cyano derivatives of tetrahydroquinolines and related compounds
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, (2008/06/13)
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.
Silicon derivatives of tetrahydroquinolines
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, (2008/06/13)
The invention relates to novel silicon derivatives of tetrahydroquinolines, which are intermediates in a process for preparing 5,6,7,8-tetrahydroquinoline-8-carboxamides and thiocarboxamides.
Certain 5,6,7,8-tetrahydroquinoline-8-thiocarboxamides
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, (2008/06/13)
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.
Cyclopenteno[b]pyridine derivatives
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, (2008/06/13)
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.
Cyclopenteno[b]pyridine derivatives
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, (2008/06/13)
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.
Pharmaceutical compositions containing 5,6,7,8-tetrahydroquinoline derivatives and related compounds
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, (2008/06/13)
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.
8-Cyano-5,6,7,8-tetrahydroquinoline derivatives
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, (2008/06/13)
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.
