A facile entry into benzo-/naphtho-pyrano-indolizino-indole through sequential intramolecular 1,3-dipolar cycloaddition and Pictet-Spengler cyclisation

Synlett

Volumn , Issue 7, 2005, Pages 1167-1169

  Subramaniyan, G ^a   Jayashankaran, Jayadevan ^a   Manian, Rathna Durga R S ^a   Raghunathan, Raghavachary ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

1,3 dipolar cycloaddition; Azomethine ylide; Intramolecular; N metallation; Pictet Spengler reaction

Indexed keywords

BENZENE DERIVATIVE; HETEROCYCLIC COMPOUND; IMINE; INDOLE DERIVATIVE; INDOLIZINE DERIVATIVE; NAPHTHYL GROUP; PYRAN DERIVATIVE; SILVER;

CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CONFERENCE PAPER; CYCLIZATION; CYCLOADDITION; DIPOLE; METALLATION; NUCLEAR OVERHAUSER EFFECT; PICTET SPENGLER REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REPRODUCIBILITY; STEREOSPECIFICITY; SYNTHESIS; TECHNIQUE;

EID: 18744366135     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-865216     Document Type: Conference Paper

References (12)

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11. 4. After the removal of solvent under reduced pressure the residue was subjected to column chromatography on silica gel eluting with petroleum ether-EtOAc (4:1) to afford cycloadduct.
12. Representative Procedure for Pictet-Spengler Cyclisation. A mixture of cycloadduct (1 mmol), the aromatic aldehyde (1 mmol) and p-toluene sulfonic acid (0.1 mmol) in dry toluene was boiled under reflux using Dean-Stark apparatus. After 24 h the solvent was removed under vacuum and the crude product was purified by flash column chromatography with petroleum ether-EtOAc (9:1) as eluent to give the Pictet-Spengler cyclised product.