1685-81-0Relevant articles and documents
CARBOXYLIC ACID COMPOUND
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, (2011/04/14)
To find a therapeutic agent and/or a preventive agent for diabetes mellitus or the like having excellent activity and safety. A compound represented by the following general formula (I), or a pharmacologically acceptable salt thereof. In the formula, X re
Aromatic Spiranes XX [1]: Syntheses of Dimethylsubstituted 2-Carboxymethyl-indan-1-ones and Benzylchlorides as Synthones for Syntheses of di- to tetramethylsubstituted Spirobiindandiones
Neudeck
, p. 185 - 200 (2007/10/03)
The isomeric dimethyl methylbenzoates 5, obtained from the bromides via Grignard reactions with dimethylcarbonate, were reduced with LiAlH4 to the hydroxymethyl derivatives 6. The latter were then transformed both to the benzylchlorides 7 (with SOCl2) and to the aldehydes 8 (with pyridinium chlorochromate). Knoevenagel-Doebner reaction of 8 afforded the acrylic acids 9 which (after hydrogenation to 11) were cyclized to the desired indanones 12 with polyphosphoric acid. On the other hand, 12c and 12e were prepared from dimethyl 3-chloropropiophenone (14) by warming with sulfuric acid. After NaH-catalyzed reaction with dimethylcarbonate, the indanones 12 gave the ketoesters 15 which then could be hydrogenated to the indanes 16. All reactions proceeded with satisfactory to excellent yields (60-90%).
Chromic Acid Oxidation of Indans and Tetralins to 1-Inadanones and 1-Tetralones Using Jones and Other Cr(VI) Reagents
Rangarajan, Radhika,Eisenbraun, E.J.
, p. 2435 - 2438 (2007/10/02)
The Jones chromic acid oxidation, ordinarily used for converting secondary alcohols to ketones, has been successfully extended to the oxidation of indans and tetralins to 1-indanones and 1-tetralones, respectively.A sixfold excess of the reagent was commonly used to ensure complete oxidation of starting material.Addition of anhydrous magnesium sulfate or oven-dried silica gel provided a yield increase of 15-20percent. 2,2'-Bipyridinium chlorochromate was also used and found to be effective in all cases, but this reagent requires a longer reaction time and a 16-fold excess.A comparison between these two reagents and CrO3 in acetic acid was made.The Jones reagent being least selective, gives the highest yield of sterically hindered monoketone from 1,2,3,4,5,6,7,8-octahydrophenanthrene.