Synthesis of a 1,3,4,5-Tetrahydropyrrolo[4,3,2-de]quinoline
✍ Scribed by Carlos Estévez; Lennart Venemalm; Mercedes Alvarez; John A Joule
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 786 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4020
No coin nor oath required. For personal study only.
✦ Synopsis
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
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## Abstract For Abstract see ChemInform Abstract in Full Text.
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
The 1:1 intermediate generated by the addition of quinoline to dialkyl acetylenedicarboxylates is trapped by 1,3-indanedione to yield dialkyl 3-spiroindanedione-1,2,3,3a-tetrahydropyrrolo[1,2-a]quinoline-1,2-dicarboxylates in good yields. The structures of these products were confirmed by NMR and si