Hydroxy tetralines

Hydroxy-tetralin bildet in entsprechender Reaktion 60% d.Th. 2-Oxo-dekalin (I) neben 30% d.Th. 4-Oxo-bicyclo[4.4.0]decen-(2) (II)1 ... 

In geteilter Zelle und 2 n Schwefelsaure laBt sich Phenol an Platin-Kathoden zu Cyclo-hexanol hydrieren (niedrige Stromdichte 56% d.Th.)6,7. Analog reagieren Methyl-phe-nole, -aniline und -benzoesauren sowie Methoxy-toluole usw.7. 1-Naphthol wird zu 7-Hydroxy-dekalin und 2-Naphthol zu 6-Hydroxy-tetralin in mittleren Ausbeuten reduziert7. 

SYNTHESIS To a solution of 49.2 g 5,6,7,8-tetrahydronaphthol (5-hydroxy-tetralin) in 100 mL MeOH, there was added 56 g methyl iodide followed by a... 

Durch Ansauem des Natronlauge-Extrakts wird als Hauptprodukt 42 g (57% d. Th.) 6-Hydroxy-tetralin (F ... 

Hydroxy-tetralin1 72 g 2-Naphthol werden wie vorstehend hydriert (statt 1 ml Essigsaue werden 2 ml 40%-ige Natronlauge zugesetzt). Die Reduktion ist bei 85° nach 2 Stdn. beendet. Die Aufarbeitung erfolgt wie vorstehend beschrieben Ausbeute 8 g (11% d.Th.) 6-Hydroxy-tetralin 50 g (67,5% d. Th.) 2-Hydroxy-tetralin Kp, 152°. 

In Abwesenheit einer Protonenquelle wird 1-Oxo-tetralin durch Lithium/fl. Ammoniak und Tetrahydrofuran als Cosolvens zum 1 -Hydroxy-tetralin reduziert5 6. 

Im Gegensatz dazu bilden 2-Naphthol und 1-Carboxy-naphthalin je zwei Produkte [2-und 6-Hydroxy-tetralin, letzteres zu 55-60% d.Th. bzw. 1- und 2-Carboxy-tetralin. 

Beilstein Handbook Reference) A13-07039 BRN 2046227 EINECS 208-459-0 1-Hydroxy-tetralin 1-Naphthalenol,... 

Oxo-tetralin ( 80% d.Th.) kann auf diesem Wege ausgehend von 2-Hydroxy-naph-thalin und Oxiran in einer Eintopfreaktion erhalten werden2. 

An important use of the Friedel-Crafts alkylation reaction is to effect ring closure. The most common method is to heat with aluminum chloride an aromatic compound having a halogen, hydroxy, or alkene group in the proper position, as, for example, in the preparation of tetralin ... 

Glennon RA et al. (1988) NAN-190 an cU ylpiperazine analog that antagonizes the stimulus effects of the 5-HTlA agonist 8-hydroxy-2-(di-n-propylamino)tetralin (8-OH-DPAT). Eur J Pharmacol 154(3) 339-341... 

The concept of extractive reaction, which was conceived over 40 years ago, has connections with acid hydrolysis of pentosans in an aqueous medium to give furfural, which readily polymerizes in the presence of an acid. The use of a water-immiscible solvent, such as tetralin allows the labile furfural to be extracted and thus prevents polymerization, increases the yield, and improves the recovery procedures. In the recent past an interesting and useful method has been suggested by Rivalier et al. (1995) for acid-catalysed dehydration of hexoses to 5-hydroxy methyl furfural. Here, a new solid-liquid-liquid extractor reactor has been suggested with zeolites in protonic form like H-Y-faujasite, H-mordenite, H-beta, and H-ZSM-5, in suspension in the aqueous phase and with simultaneous extraction of the intermediate product with a solvent, like methyl Aobutyl ketone, circulating countercurrently. 

Poland, R.E., Diminished corticotropin and enhanced prolactin responses to 8-hydroxy-2(di- -propy-lamino)tetralin in methylenedioxymethamphetamine pretreated rats, Neuropharmacology 29(11), 1099-1101, 1990. 

Table 5.1. Synthesis of tetralines by intermolecular trapping of hydroxy-o-quinodimethanes.

Partial reduction of polyarenes has been reported. Use of boron trifluoride hydrate (BF3 OH2) as the acid in conjunction with triethylsilane causes the reduction of certain activated aromatic systems 217,262 Thus, treatment of anthracene with a 4-6 molar excess of BE3 OH2 and a 30% molar excess of triethylsilane gives 9,10-dihydroanthracene in 89% yield after 1 hour at room temperature (Eq. 120). Naphthacene gives the analogously reduced product in 88% yield under the same conditions. These conditions also result in the formation of tetralin from 1-hydroxynaphthalene (52%, 4 hours), 2-hydroxy naphthalene (37%, 7 hours), 1-methoxynaphthalene (37%, 10 hours), 2-methoxynaphthalene (26%, 10 hours), and 1-naphthalenethiol (13%, 6 hours). Naphthalene, phenanthrene, 1-methylnaphthalene, 2-naphthalenethiol, phenol, anisole, toluene, and benzene all resist reduction under these conditions.217 Use of deuterated triethylsilane to reduce 1-methoxynaphthalene gives tetralin-l,l,3-yielding information on the mechanism of these reductions.262 2-Mercaptonaphthalenes are reduced to 2,3,4,5-tetrahydronaphthalenes in poor to modest yields.217 263... 

Cyano-1-hydroxy-6-me thoxy-tetralin, 52, 96 Cyanomesitylene, 50, 54 1-CYANO-6-METHOXY-3,4-DIHYDRO-NAPHTHALENE, 52, 96... 

Carli M, Tranchina S, Samanin R 8-Hydroxy-2-[di-n-propylamino)tetralin, a 5-HTj, receptor agonist, impairs performance in a passive avoidance task. Eur J Pharmacol 211 227-234, 1992... 

Tricklebank M, Forler C, Fozard J The involvement of subtypes of the 5-HTl receptor and of catecholaminergic systems in the behavioural response to 8-hydroxy-2-(di-n-propylamino) tetralin in the rat. Eur J Pharmacol 106 271-282, 1984... 

OH-DPAT = 8-Hydroxy-2-(di-n-propylamine)tetralin CP93129 = 5-Hydroxy-3(4-l,2,5,6-tetrahydropyridyl)-4-azaindole LY334370 = 5-(4-fluorobenzoyl)amino-3-(l-methylpiperidin-4-yl)-l -indole fumarate SB204741 = A/-(l-methyl-5-indolyl)-/V -(3-methyl-5-isothiazolyl)urea WAY100635 = N-tert-Butyl 3-4-(2-methoxyphenyl)piperazin-l-yl-2-phenylpropanamide. 

---