Thieno[2,3‐c]quinolines — Synthesis and Biological Investigation.

Abstract

Fused pyridine derivativesFused pyridine derivatives R 0450 Thieno[2,3-c]quinolines -Synthesis and Biological Investigation. -Compound (VIIIb) shows antimalarial activity. -(GOERLITZER*, K.; GABRIEL, B.; FROHBERG, P.; WOBST, I.; DRUTKOWSKI, G.; WIESNER, J.; JOMAA, H.;

Facile Synthesis of Phenanthridinone Alkaloids via Suzuki–Miyaura Cross‐coupling

“…Yield: 63.0 mg (53%); white solid; mp >310 °C (lit. >310 °C); Rf = 0.3 (hexane/EtOAc = 1/1). 1 H NMR (400 MHz, DMSO‐ d 6 ): δ 12.31 (s, 1H), 8.94 (dd, J = 6.1, 3.2 Hz, 1H), 8.79 (d, J = 8.0 Hz, 1H), 8.27 (dd, J = 6.1, 3.2 Hz, 1H), 7.70 − 7.68 (m, 2H), 7.65 − 7.53 (m, 2H), 7.51 − 7.35 (m, 1H).…”

“…Yield: 42.8 mg (49%); pale white solid; mp 312 − 315 °C (lit. 294 − 298 °C); Rf = 0.1 (hexane/EtOAc = 1/1). 1 H NMR (400 MHz, DMSO‐ d 6 ): δ 12.41 (brs, 1H), 11.93 (brs, 1H), 8.50 (d, J = 8.0 Hz, 1H), 8.47 (d, J = 7.8 Hz, 1H), 7.67 (d, J = 8.0 Hz, 1H), 7.54 (d, J = 8.0 Hz, 1H), 7.49 (t, J = 7.7 Hz, 1H), 7.43 (t, J = 7.8 Hz, 1H), 7.36 (t, J = 8.0 Hz, 1H), 7.34 (t, J = 8.0 Hz, 1H).…”

“…Yield: 49.2 mg (54%); beige solid; mp 252 − 254 °C (lit. 256 °C); Rf = 0.38 (hexane/EtOAc = 1/1). 1 H NMR (400 MHz, DMSO‐ d 6 ): δ 11.19 (brs, 1H), 8.50 (d, J = 2.9 Hz, 1H), 8.40 (d, J = 2.9 Hz, 1H), 8.06 (d, J = 7.8 Hz, 1H), 7.36 (dd, J = 7.8, 7.6 Hz, 1H), 7.26 (d, J = 8.0 Hz, 1H), 7.16 (dd, J = 8.0, 7.6 Hz, 1H).…”

Hendrickson‐Reagent‐Mediated Conversion of N‐Boc Carbamates to Isocyanates: Applications for the Synthesis of 3,4‐Dihydroisoquinolin‐1‐ones and Ureas

“…Thieno[2,3‐ c ]quinolin‐4(5 H )‐one (10 g) : White solid; R f =0.35 (CH 2 Cl 2 /MeOH, 40:1); 1 H NMR (CDCl 3 /[D 6 ]acetone 5:1 v/v, 300 MHz): δ =7.10 (ddd, J =1.7, 6.6, 8.2 Hz, 1 H), 7.26–7.37 (m, 2 H), 7.44–7.52 (m, 1 H), 7.62 (d, J =5.1 Hz, 1 H), 7.69 (d, J =5.4 Hz, 1 H), 7.80 ppm (d, J =7.8 Hz, 1 H); HRMS (FAB): m / z : calcd for C 11 H 8 NOS: 202.0327 [ M +H] + ; found: 202.0323.…”