42860-31-1Relevant academic research and scientific papers
INHIBITORS OF 11β -HYDROXYSTEROID DEHYDROGENASE TYPE 1
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Page/Page column 54-55, (2009/10/21)
This invention relates to novel compounds of the Formulae I or II and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof which are useful for the therapeutic treatment of diseases associated with the modulation or inhibition of 11 β-HSD l in mammals.Formula (I).
A New Synthesis of 2,2'-Disubstituted Unsymmetrical Biphenyls Based on the Intramolecular Ullmann Coupling Reaction Utilising Salicyl Alcohol as a Template
Takahashi, Masami,Ogiku, Tsuyosi,Okamura, Kimio,Da-te, Tadamasa,Ohmizu, Hiroshi,et al.
, p. 1473 - 1480 (2007/10/02)
A synthesis of 2,2'-disubstituted unsymmetrical biphenyls was examined by using the template-directed intramolecular Ullmann coupling reaction as a key step.The Ullmann coupling reaction of the diesters 1-5 showed that the most suitable ring size for the intramolecular Ullmann coupling reaction is an eleven-membered ring.On the basis of these results, salicyl alcohol was selected as a template.Acylations of salicyl alcohol by two different aroyl chlorides proceeded regioselectively in a one-pot procedure to afford the diesters 18 in good yields.The intramolecular Ullmann coupling reaction of 18 by the dropwise-addition method gave the cyclisation products 19 in high yields.Hydrogenolysis of 19 proceeded regioselectively to afford the unsymmetrical biphenyls 21 in quantitative yields, while the regioselective cleavage of the ester bonds of 19 by nucleophilic substitution reactions gave the corresponding 2,2'-disubstituted unsymmetrical biphenyls 22 and 24 in good yields.
Assymetric Synthesis of Axially Chiral, Unsymmetrical Diphenic Acids via Intramolecular Ullmann Coupling Reaction
Miyano, Sotaro,Fukushima, Hiroshi,Handa, Shigeru,Ito, Hiromitsu,Hashimoto, Harukichi
, p. 3249 - 3254 (2007/10/02)
A partical route to unsymmetrical diphenic acids is described.Successive esterification of ethylene glycol with two different 2-halobenzoyl chlorides gave the corresponding mixed diester, which was treated with copper powder in bolding DMF under dilution conditions.Silica-gel column chromatography allowed ready separation of the intramolecularly coupled cyclic diester (30-60 percent yield) from other by-products accompanying the Ullmann reaction, and alkaline hydrolysis gave unsymmetrical diphenic acid.Axially chiral, unsymmetrical diphenic acids of more than 99 percent enantiomeric excess were obtained from the reaction of mixed diesters prepared from (R)-1,1'-bi-2-naphthol.
