Synthesis of Quinolizine Derivatives. XX. Synthesis and Stereochemistry of Perhydrobenzo [c] quinolizine

Synthesis and <i>in Vivo</i> Evaluation of Novel Quinoline Derivatives as Phosphodiesterase 10A Inhibitors

“…Compound 16b was prepared from 13 and 15b 26) in a manner similar to that described for compound 16e, with a yield of 61% as a pale pink solid. …”

“…Pyrazole analogues with various linkers 16a-e were also synthesized in a similar manner from their precursors 15a-e as described in Chart 3. 26) Precursors 15c and d were synthesized via ipso-substitution reactions of 2-chloroquinoline with amines 17 and 18 respectively, and 15e was prepared via Suzuki coupling of 19 with 2-chloroquinoline.…”

Benzo- and indoloquinolizine derivatives. 13. Conformation of the perhydrobenzo[c]quinolizines

“…On the other hand, Ohki2 reported the cis-transoid-cis isomer (2b)3 as the preferred conformation for the analogous isomer of perhydrobenzo[c]quinolizine (2). This result seemed trans-cí soid-ci 1; (2a) cis-transoid-cis (2b) improbable to us since the trans-cisoid-cis conformation 2a does not experience the destabilizing allylic strain6 which occurs between the C-9 and C-10 protons and between the C-l and C-13 protons in la.…”

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

“…The cis-cisoid-trans-fused isomer would have isomerized to the more stable cis-cisoidcis-fused isomer. 10 The esterification of 11 according to the method utilized for the preparation of 5a gave 13 and 14 in a 2:1 ratio and a trace of 12.…”

“…Anal. (C2SH35N03) C, , N. 6(a)-Hydroxy-6(e)-phenyl-l,2,3,4,4a,5,7,8,9,10-decahydro-6ff-benzo[c]quinolizine (10). The reaction of phenylmagnesium bromide with 4.5 g (0.022 mol) of 9 conducted in Et20 according to the procedure of Sam and Temple13 gave 8.5 g of a mixture (tic showed three spots) which was triturated with petroleum ether to give 3.0 g (50%) of solid: mp 148-149°dec; tic showed one spot.…”