Diethyl acetylenedicarboxylate → Ethyl 7-ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylate

Participants

Reaction Steps

Treatment of 3-ethenylaniline (7 g) with diethylacetylene dicarboxylate (9.4 g), as described in Example 1b, gave ethyl 5-ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (0.16 g), mp 168°-170° C., δ (360 MHz, DMSO-d6) 1.37 (3H, t, CH3), 4.41 (2H, q, CH2), 5.25 and 5.55 (2H, 2dd, =CH2), 6.56 (1H, s, 3H), 7.38 (1H, d, 6-H), 7.62 (1H, t, 7-H), 7.90 (1H, d, 8-H), 8.15 (1H, 2d, CH=) and 11.87 (1H, bs, NH) and ethyl 7-ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (0.46 g), mp 177°-179° C., δ (360 MHz, DMSO-d6) 1.37 (3H, t, CH3),4.42 (2H, q, CH2), 5.47 and 5.99 (2H, 2d, =CH2), 6.65 (1H, bs, 3-H), 6.84 (1H, 2d, CH=), 7.54 (1H, d, 6-H) and 7.93 (1H, s, 8-H), 8.04 (1H, d, 5-H), 11.97 (1H, bs, NH).

Provenance & Evidence