Alk&ractz 6h4ethoxy4methylquinoline was converted inlo 8-melhoxy-l,3,4,S-teuahydroFyrmlo[4,3,2~e]quinoline by a six reaction sequence in which the IWI wp wm the formation of ihe indole ring. damirone B ki i batielline C Cl Me isobatzellinr C dehydrobufotenino chloride
Synthesis of 1,3,4,5-tetrahydropyrrolo-[4,3,2-de]quinolines via the vicarious nucleophilic sybstitution of hydrogen
✍ Scribed by Mieczysław Ma̧kosza; Jacek Stalewski
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- French
- Weight
- 875 KB
- Volume
- 51
- Category
- Article
- ISSN
- 0040-4020
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## Abstract A novel synthesis of the title compound was achieved by direct animation using Vicarious Nucleophilic Substitution (VNS) methodology. Reaction of 1,1,1‐trimethylhydrazinium iodide with 3,5‐dinitropyrazole in DMSO produces 4‐amino‐3,5‐dinitro‐1__H__‐pyrazole as a 1:1 crystal solvate with
5-(tert-Butoxycarbonyl)-7-methoxy-1-methyl-1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline (1b) was lithiated regioselectively at C-6 with sec-BuLi (3.0 equiv.) in the presence of water (1.0 equiv.) in ether at ^78 C. Under conventional conditions, 1b was lithiated non-regioselectively at the C-6, C-8