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Synthesis of 4-aminoguaiazulene and its δ-lactam derivatives

✍ Scribed by Alexandros Kiriazis; Ingo B. Aumüller; Jari Yli-Kauhaluoma

Publisher
Elsevier Science
Year
2011
Tongue
French
Weight
292 KB
Volume
52
Category
Article
ISSN
0040-4039

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✦ Synopsis

A method for nitrogen insertion into guaiazulene hydrocarbons is developed. A one-pot reaction of 7-isopropyl-1-methylazulene-4-carboxylic acid, diphenylphosphoryl azide, and an alcohol (MeOH, t BuOH or BnOH) affords the corresponding carbamates. Deprotection of benzyl (7-isopropyl-1-methylazulen-4yl)carbamate under basic conditions gave 4-aminoguaiazulene, which undergoes ring annulation reactions with 1,2-dicarbonyl reagents to yield tricyclic d-lactams.

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