1989 Volume 37 Issue 5 Pages 1226-1229
The catalytic hydrogenation of the cycl[3.3.3]azine derivative (6) or 1-azacycl[3.3.3]azine derivative (15) with PtO2 in tetrahydrofuran at atmospheric pressure gave the dihydrocyclazine derivative (10) or dodecahydro-1-azacycl[3.3.3]azine derivative (16), respectively. On the other hand, the catalytic hydrogenation of 6 or 19 in AcOH gave dodecahydrocyclazine (11) or dodecahydro-2-hydroxymethyl-1-azacyclazine (21), respectively. The catalytic hydrogenation of the hydrochloride 18 in MeOH gave methyl dodecahydro-5-methyl-1-azacycl[3.3.3]azine-2-carboxylate (20). Compounds 11, 20 and 21 should be useful as intermediates for the preparation of natural products, such as coccinelline and cernuine.
