Synthesis of N -Propargyl Pyrrolylamides and Theoretical Study of Pyrrolylimide Reduction by NaBH4.

SP 1 sp H NMR (600 MHz, CDCl SB 3 sb ): = 7.94 (dd, I J i = 5.4, 3.1 Hz, 2 H), 7.79 (dd, I J i = 5.5, 3.1 Hz, 2 H), 6.87 (dd, I J i = 2.8, 2.0 Hz, 1 H), 6.26 (t, I J i = 3.5 Hz, 1 H), 6.23 (dd, I J i = 3.7, 1.8 Hz, 1 H), 4.54 (d, I J i = 2.6 Hz, 2 H), 2.27 (t, I J i = 2.6 Hz, 1 H). Pyrroles 5 by Sonogashira Coupling; General Procedure 8 A stirred mixture of CuI (17 mg, 0.09 mmol), PPh SB 3 sb (90 mg, 0.34 mmol), and Pd(OAc) SB 2 sb (17 mg, 0.08 mmol) was purged with N SB 2 sb and heated to 50 °C. 2-[(1-Prop-2-yn-1-yl-1 H -pyrrol-2-yl)carbamoyl]benzyl Acetate (9) Ac SB 2 sb O (0.5 mL) and Et SB 3 sb N (1 mL) were added to a stirred solution of B 8g b (250 mg, 0.98 mmol) in CH SB 2 sb Cl SB 2 sb (15 mL). SP 1 sp H NMR (400 MHz, CDCl SB 3 sb ): = 7.95 (dd, I J i = 5.5, 3.0 Hz, 2 H, AA'BB'), 7.80 (dd, I J i = 5.5, 3.0 Hz, 2 H, AA'BB'), 7.20 (dd, I J i = 5.1, 0.9 Hz, 1 H), 7.01-6.99 (m, 1 H), 6.92 (dd, I J i = 4.9, 2.5 Hz, 1 H), 6.89 (dd, I J i = 5.4, 1.8 Hz, 1 H), 6.30 (dd, I J i = 4.9, 3.1 Hz, 2 H), 4.82 (d, I J i = 5.8 Hz, 2 H). [Extracted from the article]