Synthesis and Conformation of 1-Methyl-3, 4-benzo-7-thia-2-azabicyclo[3.3.1]nonane 7-Oxide

• Published in: Chemical & pharmaceutical bulletin Vol. 34; no. 5; pp. 1917 - 1923
• Main Authors: TERADA, YUKIMASA, TAKEUCHI, ISAO, HAMADA, YOSHIKI
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 1986; Maruzen; Japan Science and Technology Agency
• Subjects: Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; molecular mechanics calculation; Organic chemistry; Preparations and properties; Sulfur nitrogen heterocycle; Nitrogen heterocycle; Bicyclic compound; Sulfoxide; Aromatic compound; Tricyclic compound; NMR spectrum; Conformation
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.34.1917

1-Methyl-3, 4-benzo-7-thia-2-azabicyclo[3.3.1]nonane 7-oxide has been synthesized by the reaction of quinaldine with methylsulfinylmethyl carbanion, and its structure has been elucidated on the basis of spectral data and some chemical evidence. The conformation of the product has been further investigated by means of proton and carbon-13 nuclear magnetic resonance spectroscopy together with molecular mechanics calculations. The molecular mechanics calculations indicate that the stable conformer has a chair thiane ring with an equatorial sulfoxy group.