Synthesis of 6,7-benzomorphan from 4-phenylpyridine

Meta bridging reactions of electron-deficient aromatics. I. One-step synthesis of the 6,7-benzomorphan ring system. Facile preparation of potential narcotic antagonists

“…The stability of 8a and 8b, both of which can be isolated as crystalline solids, is remarkable. This is especially so since earlier proposals for the stable zwitterionic complexes [11][12][13][14] have all been shown incorrect.…”

Synthesis of metabolites of .DELTA.9-tetrahydrocannabinol

“…After 30 min, TLC showed the absence of starting material and the formation of a major product.. The mixture was washed successively with 1 N hydrochloric acid, aqueous sodium bicarbonate, and water, dried, and concentrated, to give 10.8 g of impure 11-chloro-A9-THC ethoxymethyl ether: NMR (CDC13) 0.88 (t, 7 Hz, 3 H. 5'-Me), 1.07, 1.40 (ss, CMe2), 1.24 (t, 7 Hz, OCH2C//3), 2.49 (t, 7 Hz, 2 H, l'-CH2), 3.26 (brd, 11 Hz, 1 H, 10a-CH), 3.75 (q, 7 Hz, 2 H, OC//2CH3), 4.01 (s, 2 H, CH2C1), 5.24 (s, 2 H, OCH2G), 6.33, 6.48 (ss, 2 H, ArH), 6.73 (s, 1 H, C=CH). This product (10.8 g) and tetramethylammonium acetate (10.6 g, 79.8 mmol) in acetone (125 ml) were stirred and refluxed for 21 hr, when TLC showed no starting material remained.…”

Benzo[g]quinolines. I. Synthesis and pharmacological evaluation of cis- and trans-1-alkyl-5,5-dimethyl-1,2,3,4a,5,10,10a-octahydrobenzo[g]quinolin-7-ol. A class of narcotic antagonists

“…(%,1P.--XOi-HCl) C, , X. l,2,3,4,4a,5,10,.-A mixture of 8.0 g (0.018 mole) of 4a p-toluenesulfonate, 65 ml of AcOH, and 13 ml of IPSO4 was heated on a steam bath for 10 min, poured into FPO, made basic with NI140H, and extracted with Et20. The extract was washed (HA>), dried, filtered, and evaporated to dryness to give 3.6 g (80% ) of crude 5a.…”

“…C, , N. l,2,3,4,4a,5,10,5,quinoline.-A 1.0-g sample of 5a-HCl was converted to the base with NH4OH and dried in EtA). After filtration and evaporation of the solvent, the residue (0.7 g), 2 ml of HCX)2H, and 2 ml of 356], CIPO were heated on a steam bath for 1.5 hr, diluted (1120), made basic with NH4OIl, and extracted with Kt20.…”