61417-99-0Relevant academic research and scientific papers
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.
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
