Ruthenium Tetroxide Oxidation of 1-Azabicycloalkan-2-ones

• Published in: Chem. Pharm. Bull Vol. 33; no. 11; pp. 5042 - 5047
• Main Authors: NITTA, YOSHIHIRO, ARAKAWA, YUKIMI, YOSHIFUJI, SHIGEYUKI
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 01.01.1985; 公益社団法人日本薬学会; Pharmaceutical Soc Japan; Maruzen
• Subjects: 1-azabicycloalkan-2-one; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; hydroxylation; Life Sciences & Biomedicine; Organic chemistry; oxidation; Pharmacology & Pharmacy; Physical Sciences; Preparations and properties; regioselectivity; ruthenium tetroxide; ruthenium tetroxide oxidation; Science & Technology; two-phase method; Five membered ring; Hydroxylation; Regioselectivity; Angular nitrogen heterocycle; Nitrogen heterocycle; Lactam; Imide; Six membered ring; Bicyclic compound; Oxidation; Ruthenium VIII Oxides; Infrared spectrum; NMR spectrum; Oxygen nitrogen heterocycle
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.33.5042

The ruthenium tetroxide (RuO4) oxidation of 1-azabicycloalkan-2-ones was investigated. The oxidation of quinolizidin-4-one (4), indolizidin-3-one (9), pyrrolizidin-3-one (11) and tetrahydro-1H, 3H-pyrrolo [1, 2-c] oxazol-3-one (12) occurred at the bridgehead tertiary carbon atom and afforded the corresponding hydroxy compounds (from 11 and 12) or the imidobutyric acid derivatives (from 4 and 9). This regioselectivity is contrary to the general situation in the oxidation of N-acyl cyclic amines. However, 1-azabicyclo [4.2.0] octan-8-one (17) was oxidized at the secondary carbon atom to give the 2, 8-dione (18).