Condensation of 2-Naphthol and Naphthalenediols with o-Dichlorobenzene in the Presence of Aluminum Halides | Sciact - CRIS-система Института катализа

Condensation of 2-Naphthol and Naphthalenediols with o-Dichlorobenzene in the Presence of Aluminum Halides Научная публикация

Журнал

Chemical & Pharmaceutical Bulletin
ISSN: 0009-2363 , E-ISSN: 1347-5223

Вых. Данные

Год: 2012, Том: 60, Номер: 6, Страницы: 722-727 Страниц : 6 DOI: 10.1248/cpb.60.722

Ключевые слова

2-naphthol, Naphthalenediol; tetralone, Superacid, Superelectrophilic activation

Авторы

Koltunov Konstantin Yuryevich ^1,2,3 , Chernov Aleksey Nikolaevich ^1,2 , Prakash Gubbi Krishnamurthy Surya ³ , Olah George Andrew ³

Организации

1	Boreskov Institute of Catalysis; Pr. Akademika Lavrentieva, 5, Novosibirsk 630090, Russia
2	Novosibirsk State University, Pirogova, 2, Novosibirsk 630090, Russia
3	Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California; University Park, Los Angeles, California 90089–1661, U.S.A.

Информация о финансировании (2)

1	University of Southern California
2	National Science Foundation

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.

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 & Pharmaceutical Bulletin. 2012. V.60. N6. P.722-727. DOI: 10.1248/cpb.60.722 WOS Scopus РИНЦ CAPlusCA OpenAlex

Поступила в редакцию:	14 дек. 2011 г.
Принята к публикации:	28 мар. 2012 г.
Опубликована online:	11 апр. 2012 г.
Опубликована в печати:	1 июн. 2012 г.

Web of science:	WOS:000304727000004
Scopus:	2-s2.0-84862325567
РИНЦ:	17991867
Chemical Abstracts:	2012:1233811
Chemical Abstracts (print):	157:687452
OpenAlex:	W2949287101

БД	Цитирований
Web of science	7
Scopus	8
РИНЦ	7
OpenAlex	9