Studies on the synthesis of the azocino[4,3-b]indole framework and related compounds
✍ Scribed by Nesimi Uludag; Suleyman Patir
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2007
- Tongue
- English
- Weight
- 374 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
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An efficient method for the synthesis of C‐4 position alkylated azocino[4,3‐b]indole 13 and 18 is described. Reduction of compounds 5, 6, 7 and 8 yielded the corresponding alcohols. Compounds 5, 6, 7 and 8 were synthesized through several steps starting from 1. The resulting alcohols underwent acid catalyzed ring closure to give tetracyclic azocino[4,3‐b]indole 9, 10, 11 and 12. Finally, compounds 9 and 17 were alkylated at C‐4 position to the corresponding products 13 and 18. The structure of the compounds 13 and 18 has been confirmed by X‐ray single crystal analysis.
📜 SIMILAR VOLUMES
## Abstract The synthesis of compound **12** which has a hexahydro‐1,5‐methanoazocino[4,3‐__b__]indole structure for the synthesis of pentacyclic strychnos type alkaloids (tubifolin and tubifolidine) is described. Many new compounds **5–12** have also been synthesized.
## Abstract The synthesis of some new pyrido[1′,2′:1,2]azepino[3,4‐__b__]indoles starting from indole‐3‐propanamine 1 is described. Stereochemistry and observed side reactions are discussed.
## Abstract The regio‐ and stereoselective construction of the azocino[__cd__]indole core was achieved by applying a Pd‐catalyzed intramolecular acetylene hydroarylation protocol. The applicability of a similar strategy for the synthesis of the azepino[__b__]indole framework is demonstrated.