Syntheses of Azido- and Diazido- 10-Methylacridinium Salts.

2-Azido- and 3,6-diazido-10-methylacridinium salts were synthesized in good yield from the corresponding nitro- and diaminoacridines. The synthetic scheme involved reduction of the nitro group to an amino function, acetylation of the primary amino group, methylation of the ring nitrogen with subsequent removal of the protecting group and diazotization of the primary amine followed by nucleophilic displacement of the diazonium salt with sodium azide.Synthesis of 4-azido-9-amino-10-methylacridinium chloride was unsuccessful at the methylation stage due to steric hindrance of the 4-acetamido group. An improved yield of 4-nitro-9-aminoacridine is also reported.

Level thesis:degree_level

Thesis

Year

1981

Author dc:creator

• Muschelewicz, Adana Ocak

• Synthetic scheme
• Sodium azide
• Diazotization
• Primary amino group
• Nucleophilic displacement

Repository record dc:identifier

https://digitalcommons.library.uab.edu/etd-collection/7082

OAI identifier oai:identifier

oai:digitalcommons.library.uab.edu:etd-collection-8074