A Convenient Synthesis of Tricyclic Gamma-Lactams, Simulating B-C-D Rings of Azasteroids Via Michael Addition Reaction

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• 6a, m.p. 101–1020C, IR (CHCl3) V max 1740, 1695 cm−1;1H–NMR (CDCl3 250 MHz) δ 2.54 (dd,1H,JGem = 17.7 Hz, Jvic = 9.2 Hz), 3.41 (ddd,1H), 3.5 (s,3H), 4.5 (ddd,1H), 7.2–7.4 (m,9H) ppm. 13C–NMR (CDCl3, 62.5 MHz) 37.4, 38.7, 42.8, 51.6, 64.1, 125.2, 126.7, 127.4, 129.0, 129.2, 131.6, 135.4, 142.0, 170.2, 172.7. MS(m/e) 345(M+2), 343(M), 272, 270, 213, 211, 140, 138, 117. A satisfactory elemental analysis was also obtained.
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• 8a, m.p. 189–1900C, IR (Nujol) V max 1700, 1675 cm−1, 1H–NMR (CDCl3, 200 MHz): 2.6 (m,4H), 3.40 (m,1H), 4.30 (m,1H), 7.2–7.6 (m,6H), 8.0 (m,1H), 8.8 (d,1H) ppm. 13C-NMR Spectrum (CDCl3, 25 MHz): 39.9, 42.8, 45.7, 63.2, 120.5, 126.9, 127.2, 127.9, 129.1, 129.6, 135.0, 137.8, 139.4, 172.0, 190.5, MS(m/e) 311(M+). The compound gave satisfactory elemental analyses.
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