405196-36-3Relevant articles and documents
Synthesis of functionalized difluoronaphthalenes by regioselective C—H functionalization of 2,3-difluoronaphthalene
Volchkov,Lipkind,Nefedov
, p. 270 - 279 (2020)
2,3-Difluoronaphthalene (1) was selectively converted into 1-methyl-, 1,4-dimethyl-, 1-acetyl-, 1-acetyl-4-methyl-, 1-formyl-, and 1-carboxyl-substituted 2,3-difluoronaphthalenes using lithiation with BuLi as a key step. Nitration and bromination of compound 1 predominantly gave 6,7-difluoro-1-nitronaphthalene and 1-bromo-6,7-difluoronaphthalene, respectively. Regioselectivity of acylation of compound 1 and 2,3-difluoro-1,4-dimethylnaphthalene with AcCl in the presence of AlCl3 dramatically depended on the order of mixing and addition of the reagents. Under the optimized conditions, the yields of 1-(6,7-difluoronaphthalen-1-yl) ethanones and 1-(6,7-difluoronaphthalen-2-yl)ethanones reached 68–93%.
A simple route to 6- and 7-fluoro-substituted naphthalene-1-carboxylic acids
Krülle, Thomas M.,Barba, Oscar,Davis, Susan H.,Dawson, Graham,Procter, Martin J.,Staroske, Thomas,Thomas, Gerard H.
, p. 1537 - 1540 (2008/02/02)
A simple one-pot method for the synthesis of 6-fluoro- and 6,7-difluoro-1-naphthoic acid is described. 6-Fluoro-1-naphthoic acid can be converted into 7-fluoro-1-naphthoic acid in three straightforward steps.
DIHYDROIMIDAZOTHIAZOLE DERIVATIVES
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Page/Page column 64, (2008/06/13)
Compounds of formula (I): or pharmaceutically acceptable salts thereof, exhibit 5-HT1A agonism in addition to noradrenaline reuptake inhibition and optionally also 5-HT reuptake inhibition are useful for the treatment of obesity.
Synthesis of mono- and difluoronaphthoic acids
Tagat, Jayaram R.,McCombie, Stuart W.,Nazareno, Dennis V.,Boyle, Craig D.,Kozlowski, Joseph A.,Chackalamannil, Samuel,Josien, Hubert,Wang, Yuguang,Zhou, Guowei
, p. 1171 - 1177 (2007/10/03)
Aryl carboxamides are useful structural units found in several biologically active compounds. Unlike their benzoic acid counterparts, fluorinated versions of naphthoic acids are relatively unknown. In connection with a recent project, we needed viable syntheses of several mono- and difluorinated naphthoic acids. Herein we describe the synthesis of 5-, 6-, 7-, and 8-fluoro-1-naphthalenecarboxylic acids and 5,7-, 5,8-, 6,7-, and 4,5-difluoro-1-naphthalenecarboxylic acids. The 5-fluoro derivative 1 was obtained from the corresponding 5-bromo compound via electrophilic fluorination of the lithio-intermediate. The rest of the monofluoro (2, 3, and 4) and the difluoro acids (5, 6, and 7) were prepared by a new, general route which entailed the elaboration of commercial fluorinated phenylacetic acids to 2-(fluoroaryl)glutaric acids with differential ester groups; selective hydrolysis to a mono acid, intramolecular Friedel-Crafts cyclization, and aromatization furnished the target structures. An alternative process to assemble a naphthalene skeleton is also presented for the difluoro acids 5 and 6. Finally, 4,5-difluoro-1-naphthalenecarboxylic acid (8) was prepared expeditiously from 1,8-diaminonaphthalene by adapting classical reactions.