Инд. авторы:	Koltunov K.Y., Chernov A.N., Prakash G.K.S., Olah G.A.
Заглавие:	Condensation of 2-naphthol and naphthalenediols with o-dichlorobenzene in the presence of aluminum halides
Библ. ссылка:	Koltunov K.Y., Chernov A.N., Prakash G.K.S., Olah G.A. Condensation of 2-naphthol and naphthalenediols with o-dichlorobenzene in the presence of aluminum halides // Chemical and Pharmaceutical Bulletin. - 2012. - Vol.60. - Iss. 6. - P.722-727. - ISSN 0009-2363.
Внешние системы:	PubMed: 22689422; SCOPUS: 2-s2.0-84862325567;
Реферат:	eng: It is known that 1-naphthol, as a result of superelectrophilic (dicationic) activation in superacid media, is able to react with such deactivated aromatic compound as o-dichlorobenzene to give 4-(3,4-dichlorophenyl)-1-tetralone (2), which is a highly valuable intermediate in the synthesis of the antidepressant, sertraline (1) and other useful derivatives. However, the analogous reactivity of 2-naphthol and a variety of naphthalenediols towards o -dichlorobenzene has not been investigated thus far, although the corresponding tetralones, bearing dichlorophenyl moiety, could be of great pharmacochemical interest. In present work, we disclose that 1,5-, 1,6-, and 1,7- naphthalenediols (6a-c) react smoothly with o -dichlorobenzene in the presence of an excess of aluminum chloride or aluminum bromide to give the pairs of isomeric 4-(3,4- dichlorophenyl)- and 4-(2,3-dichlorophenyl)- 5-, 6-, and 7-hydroxy-1-tetralones (10a-c and 11a-c) in high overall yields. 2-Naphthol and 2,7-naphthalenediol (6d) exhibited comparatively lower reactivity, which however was sufficient to obtain the corresponding dichlorophenyl-2-tetralones in moderate yields. The mechanism of these reactions involving superelectrophilic dicationic or even tricationic intermediates, is discussed. © 2012 The Pharmaceutical Society of Japan.
Ключевые слова:	4 (2,3 dichlorophenyl) 6 hydroxy 1 tetralone; 4 (2,3 dichlorophenyl) 7 hydroxy 1 tetralone; 4 (3,4 dichlorophenyl) 1 tetralone; 4 (3,4 dichlorophenyl) 5 hydroxy 1 tetralone; 4 (3,4 dichlorophenyl) 6 hydroxy 1 tetralone; 4 (3,4 dichlorophenyl) 7 hydroxy 1 tetralone; aluminum chloride; aluminum derivative; aromatic compound; naphthalene derivative; sertraline; unclassified drug; article; chemical reaction; drug structure; drug synthesis; electrophilicity; polymerization; quantum yield; reaction analysis; Tetralones; Stereoisomerism; Naphthols; Molecular Structure; Chlorobenzenes; Chlorides; Aluminum Compounds; 4 (2,3 dichlorophenyl) 1 tetralone; 2 naphthol; 1,2 dichlorobenzene; 1 tetralone derivative; Superelectrophilic activation; Superacid; tetralone; Naphthalenediol; 4 (2,3 dichlorophenyl) 5 hydroxy 1 tetralone; 2-naphthol;
Издано:	2012
Физ. характеристика:	с.722-727