Studies on Quinolizine Derivatives. XXIV. : Catalytic Hydrogenation of Cycl[3.3.3]azines

• Published in: Chemical & pharmaceutical bulletin Vol. 37; no. 5; pp. 1226 - 1229
• Main Authors: MATSUDA, Yoshiro, GOTOU, Hiromi, KATOU, Keisuke, MATSUMOTO, Hiroshi
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 1989; Maruzen
• Subjects: antiaromatic character; azacycl[3.3.3]azine; cernuine; Chemistry; coccinelline; cycl[3.3.3]azine; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; hydroazacycl[3.3.3]azine; hydrocycl[3.3.3]azine; Organic chemistry; Preparations and properties; Solvent effect; Platinum IV Oxides; Catalytic reaction; Cyclazine; Angular nitrogen heterocycle; Acetic acid; Tricyclic compound; Hydrogenation
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.37.1226

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.