Tetralins methoxy

A remarkable feature of the Birch reduction of estradiol 3-methyl ether derivatives, as well as of other metal-ammonia reductions, is the extreme rapidity of reaction. Sodium and -butyl alcohol, a metal-alcohol combination having a comparatively slow rate of reduction, effects the reduction of estradiol 3-methyl ether to the extent of 96% in 5 minutes at —33° lithium also effects complete reduction under the same conditions as is to be expected. Shorter reaction times were not studied. At —70°, reduction with sodium occurs to the extent of 56 % in 5 minutes, although reduction with lithium is virtually complete (96%) in the same time. (The slow rates of reduction of compounds of the 5-methoxytetralin type is exemplified by 5-methoxy-tetralin itself with sodium and f-butyl alcohol reduction occurs to the extent of only 50% in 6 hours vs. 99+% with lithium.) The iron catalyzed reaction of sodium with alcohols must be very fast since it competes so well with the rapid Birch reduction. One cannot compensate for the presence of iron in a Birch reduction mixture containing sodium by adding additional metal to extend the reaction time. The iron catalyzed sodium-alcohol reaction is sufficiently rapid that the aromatic steroid still remains largely unreduced. 

Methoxy-2-(2-amino-benzoylhydrazino)-tetralin 8-Methoxy-2- pyridyl-(4)-carbonylhydrazino]-tetralin... 

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. 

The lack of clear-cut hallucinogen-type activity for the 2-aminotetralins could be explained in several ways. The known deleterious effect of molecular bulk in the alpha-position would seem to direct attention to the steric effect of the reduced ring of the tetralins as detrimental to activity. In 18b, however, it has been noted (156) that the 5-methoxy group is forced out of plane by the adjacent 6-methyl and 4-methylene groups. The importance to activity of maintaining the methoxy groups coplanar with the aromatic ring has been emphasized earlier. Both substituent orientation and N-alkylation must also be important to activity, and it may not be realistic to make direct comparisons between the phenethyl-amines and the 2-aminotetralins. 

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

Fithium tetrahydroaluminate, Fluoroamides, 0075 Lithium tetrahydroaluminate, Water, 0075 Lithium, 1,2-Diaminoethane, Tetralin, 4675 Magnesium, Barium carbonate, Water, 4685 Maleic anhydride, Bases, or Cations, 1400 Mercaptoacetonitrile, 0763 t Methanol, Hydrogen, Raney nickel catalyst, 0482 4-Methoxy-3-nitrobenzoyl chloride, 2911 Methoxyacetyl chloride, 1161 t Methyl formate, Methanol, Sodium methoxide, 0830 3-Methyl-2-penten-4-yn-l-ol, 2378 Nitric acid, 4430... 

Quinolin 4-(2-Hydroxy-ethyl)-1,2,3,4-tetrahydro- XI/1, 729 Tetralin 5-Amino-6-methoxy- XI/1, 690... 

Tetralin 8-Chlor-2-hydroxy-5-methoxy-2-methyl-l-oxo- E21e, 4514 (H - OH)... 

Aziridin l-tert.-Butyl-2-oxo-3-phenyl- E16b, 7 (aus Br — CR2 — CO — NHR), 10 (aus R2CH-CO-NR-Cl) 5H-1-Benzazepin 7-Methoxy-2-methyl-3,4-dihydro- E14b, 234 (Tetralin 4 HN3)... 

H-Pyran 6-Ethoxy-5-phenoxy-5,6-dihydro- VI/4, 362 Tetralin 2-Carboxymethyl-6-methoxy- IV/lc, 713 Tricyclo[4.3.2.02 5]undec-10-en ... 

Eudalene sesquiterpenes. Syntheses of eudalene-type sesquiterpenes commonly utilize the Robinson annelation reaction to construct the bicyclic ring system. However, this annelation reaction often proceeds in low yields and with stereochemical difficulties. Huffman and Mole10 have recently reported a new stereoselective synthesis. 8-Methoxy-tetralin-2-carboxylic acid (1) is reduced under Birch conditions followed by acid... 

Methoxy-benzoyl)-l-(4-methoxy-phenyl)- 2056. 2081 2-(4-Metlioxy-benzoyl)-l-(3-methoxy-phcnyl)- 2056, 2081 2-(4-Methoxy-bcnzoyl)-l-(4-methoxy-phenyl)- 2081 Tetraline... 

Dimethoxy-phenylthio)-1 -(1 -hydroxy-6-methoxy-tetralin-2-ylidenemethyl)- 2425... 

Gegensatz dazu ergeben 1,5- und 1,6-Dihydroxy-naphthaline als Hauptprodukte 5-Hydroxy-1 -oxo- (isoliert als 5-Methoxy-Derivat F 87-88°) bzw. 6-Hydroxy-1 -oxo-tetralin (F 150-152°). 

Aus 6-Methoxy-l-oxo-2-carboxymethylen-tetralin entstehen 96% d. Th. 6-Methoxy-2-carboxymethyl-tetralin (F 93—94°)5 ... 

In the mass spectra of compounds (1 5) and (36), as shown in Chart 8, not only the molecular ion peaks at m/z 428 but also other prominent ion peaks at m/z 260, 215, 203, 181 and 168 were common to both compounds. The mass spectra of analogous lignans have been reported by Duffield and Pelter (ref. 38). Therefore each fragment ion was assigned as shown in Chart 8b. The above results show that compound (1 5) has a trimethoxyphenyl group and a tetralin ring, and that a methoxy and a methylenedioxy group on the benzene nucleus. 

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