Synthesis of novel indole based cyclophanes and cylindrical cyclophanes by tandem alkylation methodology using NaH

Tetrahedron Letters

Volumn 47, Issue 18, 2006, Pages 3019-3022

  Rajakumar, Perumal ^a   Gayatri Swaroop, Merikapudi ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BIS(BROMOMETHYL)BENZENE; 1,3,5 TRIMETHYL 2,4,6 TRIS(BROMOMETHYL)BENZENE; 1,3,5 TRIS(BROMOMETHYL)BENZENE; 2,6 BIS(BROMOMETHYL)PYRIDINE; BENZENE DERIVATIVE; CYCLOPHANE DERIVATIVE; INDOLE; PYRIDINE DERIVATIVE; SODIUM DERIVATIVE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; METHODOLOGY; SYNTHESIS;

EID: 33645843631     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.013     Document Type: Article

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26. 2: C, 87.64; H, 5.98; N, 6.39. Found: C, 87.78; H, 5.89; N, 6.44.
27. 2: C, 85.68; H, 5.99; N, 8.33. Found: C, 85.74; H, 6.02; N, 8.29.
28. 4: C, 81.79; H, 5.49; N, 12.72. Found: C, 81.73; H, 5.56; N, 12.67.
29. 3: C, 81.87; H, 5.68; N, 12.45. Found: C, 81.85; H, 5.71; N, 12.43.
30. 3: C, 86.84; H, 6.83; N, 6.33. Found: C, 86.76; H, 6.86; N, 6.37.
31. 3: C, 85.17; H, 6.55; N, 8.28. Found: C, 85.14; H, 6.51; N, 8.32.
32. 3: C, 87.01; H, 5.74; N, 7.25. Found: C, 87.05; H, 5.78; N, 7.22.
33. 3: C, 85.13; H, 5.85; N, 9.03. Found: C, 85.16; H, 5.82; N, 9.08.
34. 3-hexane (1:3) as eluent to give indolophanes 1 and 2 as light sensitive white solids.
35. An identical procedure was adopted for the syntheses of cylindrical cyclophanes 3 and 4, which were obtained as light sensitive white solids. Reagents: NaH (16.5 mmol) in 20 mL THF; indole (1.1 mmol) in 30 mL THF and tribromide (1.2 mmol) in 200 mL THF.