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New entry to bridged pentacyclic indolyltetrahydroisoquinoline skeleton via tandem s-alkylation and intramolecular C-Alkylation

Matloubi Moghaddam, F ; Sharif University of Technology | 2010

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  1. Type of Document: Article
  2. DOI: 10.1055/s-0029-1218534
  3. Publisher: 2010
  4. Abstract:
  5. An efficient, single-step synthesis of hitherto unknown indole-annulated pentacyclic indolylhydroisoquinolines via tandem S-alkylation and intramolecular C-alkylation of indolin-2-thiones with N-alkylisoquinolinium salts is reported. This new approach provides a powerful entry into polycyclic structures containing nitrogen and sulfur related to alkaloids
  6. Keywords:
  7. Indolyltetrahydroisoquinoline ; Isoquinolinium salts ; Pentacyclic heterocycles ; Tandem reaction ; Thiooxindoles ; 14 allyl 5 methyl 5,7,12,13 tetrahydro 7,13 epimino[2]benzothiocino[3,4 b]indole ; 14 benzyl 5,7,12,13 tetrahydro 7,13 epimino[2]benzothiocino[3,4 b]indole ; 14 ethyl 5 methyl 5,7,12,13 tetrahydro 7,13 epimino[2]benzothiocino[3,4 b]indole ; 14 ethyl 5 phenyl 5,7,12,13 tetrahydro 7,13 epimino[2]benzothiocino[3,4 b]indole ; 14 ethyl 5,7,12,13 tetrahydro 7,13 epimino[2]benzothiocino[3,4 b]indole ; 14 methyl 5 phenyl 5,7,12,13 tetrahydro 7,13 epimino[2]benzothiocino[3,4 b]indole ; 14 methyl 5,7,12,13 tetrahydro 7,13 epimino[2]benzothiocino[3,4 b]indole ; 14 prop 2 yn 1 yl 5,7,12,13 tetrahydro 7,13 epimino[2]benzothiocino[3,4 b]indole ; 5 ethyl 14 methyl 5,7,12,13 tetrahydro 7,13 epimino[2]benzothiocino[3,4 b]indole ; 5,14 diethyl 5,7,12,13 tetrahydro 7,13 epimino[2]benzothiocino[3,4 b]indole ; 5,14 dimethyl 5,7,12,13 tetrahydro 7,13 epimino[2]benzothiocino[3,4 b]indole ; Indole derivative ; Isoquinoline derivative ; Pentacyclic indoyltetrahydroisoquinoline ; Unclassified drug ; Acylation ; Alkylation ; Carbon nuclear magnetic resonance ; Chemical analysis ; Chemical reaction ; Chemical structure ; Intramolecular C alkylation ; Proton nuclear magnetic resonance ; Synthesis ; Tandem S alkylation
  8. Source: Synlett ; Issue 1 , 2010 , Pages 123-127 ; 09365214 (ISSN)
  9. URL: https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0029-1218534