Quinolines Reimer-Tiemann reaction

Ring expansion during Reimer-Tiemann reaction conditions on pyrroles and indoles to furnish pyrid-ines and quinolines was observed by Ciamician in 1881 (equations 13 and 14). Although a preparative reaction of little use due to the low yield, this transformation stimulated others to carry out ring expansion attempts on nonphenolic substrates with considerable success. ... 

Pyrrolenines, intermediates in Reimer-Tiemann reaction of pyrroles, 72 pyridines from, 72 ring expansion of, 72 structures of, 72 3H-Pyrrolo[2,3-c]quinoline, 93 Pyrroloquinolones, 169... 

The idea that dichlorocarbene is an intermediate in the basic hydrolysis of chloroform is now one hundred years old. It was first suggested by Geuther in 1862 to explain the formation of carbon monoxide, in addition to formate ions, in the reaction of chloroform (and similarly, bromoform) with alkali. At the end of the last century Nef interpreted several well-known reactions involving chloroform and a base in terms of the intermediate formation of dichlorocarbene. These reactions included the ring expansion of pyrroles to pyridines and of indoles to quinolines, as well as the Hofmann carbylamine test for primary amines and the Reimer-Tiemann formylation of phenols. 

The Reimer-Tiemann formylation of several phenols in the quinoline and pyrimidine series is known, but the reaction is unsuccessful with hydroxjrpyridines 3-hydroxypyridine gave a polymer. No 2-hydroxyquinoline appears to have been studied the 4-hydroxy... 

---