SNH‐ and SNipso‐Arylamination of 1, 3, 7‐Triazapyrenes. Issue 34 (21st October 2014)

• Record Type: Journal Article
• Authors: Borovlev, Ivan; Demidov, Oleg; Saigakova, Nadezhda; Amangasieva, Gulminat
• Is Part Of: European journal of organic chemistry. Issue 34(2014)
• Page Start: 7675
• Page End: 7683
• Publication Date: 2014-10-21
• Subjects: Amination -- Aromatic substitution -- Nucleophilic substitution -- Nitrogen heterocycles -- Polycycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402891
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The ability of the oxidative arylamination process to derivatize electron‐deficient 1, 3, 7‐triazapyrenes has been investigated. These triazapyrenes react with a wide range of sodium aryl(hetaryl) amides to give access to the corresponding 6‐aryl(hetaryl)amino‐1, 3, 7‐triazapyrenes in moderate to good yields. The reaction of 6, 8‐dialkoxy‐1, 3, 7‐triazapyrene with sodium arylamides gives rise to 6, 8‐bis(arylamino)‐1, 3, 7‐triazapyrenes or 6‐methoxy‐8‐arylamino‐1, 3, 7‐triazapyrenes, depending on the reaction conditions. Abstract : 6‐Arylamino‐1, 3, 7‐triazapyrenes were obtained from 1, 3, 7‐triazapyrenes through an oxidative SN H ‐process, whereas 6, 8‐bis(arylamino)‐1, 3, 7‐triazapyrenes and 6‐alkoxy‐8‐arylamino‐1, 3, 7‐triazapyrenes were synthesized from 6, 8‐dialkoxy‐1, 3, 7‐triazapyrenes, using SN ipso methodology. In all cases, the corresponding sodium arylamides were used as reactants.