Synthesis of functionalized tetrahydroisoquinolines via palladium-catalyzed 6-exo-dig carbocyclization of 2-bromo-N-propargylbenzylamines

Tetrahedron Letters

Volumn 52, Issue 14, 2011, Pages 1644-1648

  Nandakumar, A ^a   Muralidharan, D ^a   Perumal, P T ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

6 exo dig regiochemistry; A3 coupling; Carbocyclization; Palladium; Tetrahydroisoquinolines

Indexed keywords

ALDEHYDE; ALKYNE; AMINE; PALLADIUM; TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; CYCLIZATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 79952360554     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.127     Document Type: Article

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28. General procedure for the synthesis of propargylamine (4): A mixture of CuI (15 mol %), amine (0.50 mmol), aldehyde (0.55 mmol) and phenylacetylene (0.75 mmol) in toluene (3 mL) was heated at 100 °C for 3 h. Then the reaction mixture was filtered through Celite and washed with ethyl acetate. After removal of the solvent, the residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate as eluent, affording compound in good yield (shown in Table 2).
29. 26BrNO: C, 72.58; H, 5.28; N, 2.82. Found: C, 72.62; H, 5.26; N, 2.85.
30. 4) and concentrated under reduced pressure. The crude product was chromatographed (petroleum ether/ethyl acetate as eluent) and its appropriate yield is shown in Table 4.
31. 27NO: C, 86.30; H, 6.52; N, 3.35. Found: C, 86.33; H, 6.55; N, 3.33.