Unusual hydrolysis of 2-nitrosopyridines. Formation of 1-(2-pyridyl)-2(1H)-pyridones

An improved Ullmann–Ukita–Buchwald–Li conditions for CuI-catalyzed coupling reaction of 2-pyridones with aryl halides

“…calcd for C12 H 10 BrNO 2 C, 51.45;H, 3.60; N, 5.00. Found C, 51.19;H, 3.58; N,phenyl)pyrid-2-one(15).Reaction time: 24 h, white solid (59%). Mp 220-221 8C (from CH 2 Cl 2 /hexaneZ1:10); 1 H NMR (400 MHz, d 6 -acetone) d 7.56 (ddd, JZ6.4, 2.4, 0.8 Hz, 1H), 7.44 (ddd, JZ9.2, 6.7, 2.4 Hz, 1H), 7.29-7.36 (m, 6H), 7.05-7.13 (m, 8H), 6.44 (dd, JZ9.2, 0.8 Hz, 1H), 6.26 (td, JZ6.7, 1.2 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) d 162.…”

Catalytic, Highly Enantio, and Diastereoselective Nitroso Diels−Alder Reaction

“…2-Nitrosopyridine was prepared in two steps from 2-aminopyridine simply following the reported procedure. 2c, We chose for initial investigations the hetero Diels−Alder reaction of cyclohexadiene with ( S )-BINAP−Cu(I)PF 6 (MeCN) 4 catalyst 5 since copper coordination to nitroso derivative is well-known . The reaction was conducted at −85 °C and gradually warmed to −20 °C to produce the adduct 3a in quantitative yield with 59% ee.…”