Condensation of 2-Naphthol and Naphthalenediols with <i>o</i>-Dichlorobenzene in the Presence of Aluminum Halides
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- Koltunov Konstantin Yuryevich
- Boreskov Institute of Catalysis Novosibirsk State University Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California
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- Chernov Aleksey Nikolaevich
- Boreskov Institute of Catalysis Novosibirsk State University
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- Surya Prakash Gubbi Krishnamurthy
- Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California
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- Olah George Andrew
- Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California
Bibliographic Information
- Other Title
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- Condensation of 2-Naphthol and Naphthalenediols with o-Dichlorobenzene in the Presence of Aluminum Halides
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Description
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.
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 60 (6), 722-727, 2012
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390282679155516544
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- NII Article ID
- 130001852471
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- NII Book ID
- AA00602100
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- COI
- 1:STN:280:DC%2BC38jgvFarsw%3D%3D
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 023665911
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- PubMed
- 22689422
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- Abstract License Flag
- Disallowed