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Volumn , Issue 1, 2009, Pages 97-99

Palladium-catalysed cascades triggered by dehydrogenation of secondary or tertiary amines: Access to bridged- and fused-ring heterocycles

Author keywords

Cascade reaction; Dipolar cycloaddition; Hydrogen transfer; Mannich reaction

Indexed keywords

EID: 62349126919 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087480 Document Type: Article

Times cited : (17)

References (16)

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16
- 62349103715
- 2-Benzo-4,7-imino-4-methoxycarbonyl-exo-6- benzyloxycarbonylcyclohept-1-ene (7) Methyl 1,2,3,4-tetrahydroisoquinoline- 3-carboxylate (1, 0.1 g, 0.5 mmol, benzyl acrylate (0.17 g, 1.0 mmol, and Pd black (0.0055 g, 0.05 mmol) were mixed in toluene (15 mL) and heated at 110°C for 15 h. After removal of the solvent the residue was purified by column chromatography eluting with Et2O-PE (1:1, v/v) to afford 7 (0.091 g, 50, as a colourless semisolid and 8 (10, Anal. Calcd, ) for C21H21NO4: C, 71.79; H, 5.98; N, 3.99. Found: C, 71.70; H, 6.20; N, 4.05. 1H NMR (300 MHz, CDCl 3, δ, 7.15-7.07 (m, 4 H, ArH, 5.12 (s, 2 H, CH 2Ph, 4.57 (s, 1 H, Ha, 3.79 (s, 3 H, CO2Me, 3.26 (d, 1 H, J, 16.60 Hz, ArCHH, 3.14 (dd, 1 H, J, 8.85, 2.60 Hz Hb, 3.02 (d, 1 H, J, 16.60 Hz, ArCHH, 2.47 dd, 1 H
- +], 292 (3), 260 (0.4), 189 (100), 157 (18).

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