Studies on organometallic compounds. III. Reaction of trimethylstannylazines with acyl chlorides. A novel C-C bond formation of pyridine nuclei.

Abstract

Introduction of an acyl group at the α-, β-, and γ-positions of pyridine nuclei was accomplished. 2-Trimethylstannyl-pyridine and -quinoline and 1-trimethylstannyliso-quinoline directly reacted with various acyl chlorides to give the corresponding 2-pyridyl, 2-quinolyl, and 1-isoquinolyl ketones, respectively. Reaction of 3-trimethylstannyl-pyridine, -quinoline, and -isoquinoline with acyl chlorides proceeded smoothly under catalysis by PdCl2 or PdCl2 (PPh3)2 to afford the corresponding ketones in good yields. Similarly, 4-pyridyl, -quinolyl, and -isoquinolyl ketones were prepared from the corresponding 4-trimethylstannyl derivatives and acyl chlorides.