Synthesis of 4-aminoguaiazulene and its δ-lactam derivatives |
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| Authors: | Alexandros KiriazisIngo B Aumüller Jari Yli-Kauhaluoma |
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| Institution: | Division of Pharmaceutical Chemistry, Faculty of Pharmacy, PO Box 56 (Viikinkaari 5 E), FI-00014 University of Helsinki, Finland |
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| Abstract: | 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, tBuOH or BnOH) affords the corresponding carbamates. Deprotection of benzyl (7-isopropyl-1-methylazulen-4-yl)carbamate under basic conditions gave 4-aminoguaiazulene, which undergoes ring annulation reactions with 1,2-dicarbonyl reagents to yield tricyclic δ-lactams. |
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| Keywords: | Azulene Conjugation Amine Heterocycle Lactam |
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