Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 65, No. 7, 2005, pp.1577-1588
Published online, 28th April, 2005
DOI: 10.3987/COM-05-10370
4-Substituted 3-Methylsulfanyl-5-, 6-, and 8-nitroquinolines from Nitro Derivatives of 4-Substituted 3’-Methylsulfinyl-3,4’-diquinolinyl Sulfides

Magdalena Kosiecka, Andrzej Maslankiewicz,* and Maria J. Maslankiewicz

*Department of Organic Chemistry, The Medical University of Silesia, Jagiellonska Str. 4, 41-200 Sosnowiec, Poland

Abstract

Potassium phenoxide reacted with 4-substituted 3’-methylsulfanyl-3,4’-diquinolinyl sulfides (1 or 3) at the substituent at the C4 position. 3’-Methylsulfinyl group promotes nucleophilic substitution of 4’-quinolinyl sulfur bond in sulfoxides (2) and (4) in which case, after treatment with potassium phenoxide, it led to 4-phenoxy-3-methylsulfinylquinoline (9) and 4-substituted 3-quinolinethiolates (5A, 6A or 7A), trapped by methylation to form 4-substituted 3-methylsulfanylquinolines (5a), (6a) and (7a) or their 5-, 6- and 8-nitro derivatives (5b,c), (6b,d) and (7b,d), respectively. Synthesis of 5-, 6- and 8-nitro-3-methylsulfanyl-4(1H)-quinolinones (10b,c,d) was described.