Synthesis in the Emetine Series XV¹) Friedel-Crafts Acylation of N-Acetylhomoveratrylamine: A Facile Synthesis of 9,10-Dimethoxybenzo[a]Quinolizidine

Metalation vs Nucleophilic Addition in the Reactions of N-Phenethylimides with Organolithium Reagents. Ready Access to Isoquinoline Derivatives via N-Acyliminium Ions and Parham-Type Cyclizations

“…9,10-Dimethoxy-2,3,6,7-tetrahydrobenzo[ a ]quinolizin-4(4 H )-one (4b). Spontaneous dehydration of 14b (230 mg) in CHCl 3 solution (1 mL) at 20 °C gave pyrroloisoquinolone 4a (210 mg, quantitative), whose data are identical to those reported in literature: 1 H NMR (CDCl 3 ) 2.34−2.42 (m, 2H), 2.48−2.51 (m, 2H), 2.73 (t, J = 5.7 Hz, 2H), 3.81−3.86 (m, 2H)*, 3.84 (s, 3H)*, 3.86 (s, 3H)*, 5.65 (t, J = 4.8 Hz, 1H), 6.58 (s, 1H), 6.99 (s, 1H) (* designates partially overlapped signals); 13 C NMR (CDCl 3 ) 19.4, 28.6, 31.1, 38.3, 55.8, 55.9, 100.5, 106.8, 110.5, 122.3, 127.1, 135.5, 147.9, 146.1, 169.9.…”

Michael Reactions of Arylidenesulfonylacetonitriles. A New Route to Polyfunctional Benzo[a]quinolizines

“…High yielding syntheses of polyfunctional benzo[ a ]quinolizines are well documented [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 ]. As a continuation of our work on the use of isoquinoline and its derivatives for the synthesis of fused heterocyclic compounds [ 10 , 11 ], we now report a new and general one step route affording polyfunctional substituted benzo[ a ]quinolizines in good yield from readily available inexpensive starting materials, which competes favorably with the methods previously reported for the preparation of the title compounds.…”