110931-79-8Relevant articles and documents
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.
Synthesis and Structure-Activity Relationships of Naphthalene-Substituted Derivatives of the Allylamine Antimycotic Terbinafine
Nussbaumer, Peter,Dorfstaetter, Gerhard,Leitner, Ingrid,Mraz, Karin,Vypel, Hermann,Stuetz, Anton
, p. 2810 - 2816 (2007/10/02)
Derivatives of the allylamine antimycotic terbinafine (1) with varied substitution at the naphthalene ring system have been prepared, and their antifungal activity has been evaluated.In general, the potency is strongly dependent on the bulkiness of the su
