1‐Arylquinolizidines

Abstract

The reaction of arylmagnesium bromides with 1‐ketoquinolizidine provided predominantly 1(e)‐aryl‐1(a)‐hydroxyquinolizidines. Dehydration of the latter and subsequent hydrogenation yielded 1‐arylquinolizidines.

Synthesis and Pharmacology of Site-Specific Cocaine Abuse Treatment Agents: Restricted Rotation Analogues of Methylphenidate

“…Chemistry. Two different synthetic pathways were designed to build the 1-aza-5-phenyl[4.4.0]decane structure . The first (Scheme ) was based on a Wittig reaction in which a carboethoxy ylide (Ph 3 PCHCO 2 Et) was utilized to incorporate two additional carbon atoms into MP at the ester carbonyl carbon.…”

6-Phenyl-6-propionoxyperhydrobenzo[c]quinolizines as potential analgetics

“…Anal. (C19H27NO) C, , N. cis-transoid-trans-6-Phenyl-1,2,3,4,4a, 6a, 7,8,9,10,10a-dodecahydro-lH-benzo[c]quinolizine (13) and cis-transoid-trans-fi-Chloro-6-phenylperhydrobenzo[c]quinolizine (14) from the Attempted Esterification of 11. A mixture of 7.1 g (0.022 mol) of the hydrochloride of 11, 250 ml of MeCN, and 50 ml of propionyl chloride was heated at 60-70°for 12 hr.…”

3-Aryl-3-hydroxyquinolizidines with potential hypotensive, antidepressant, and analgetic activity

“…This was in contrast to the predominance of equatorial aryl isomers obtained in a related series of 1aryl-1 -hydroxyquinolizidines prepared from 1-ketoquinolizidine. 4 The latter was explained on the basis of complexation between the Grignard reagent and the nitrogen tThis investigation was supported in part by NIMH Grant No. MH 16973.…”