Synthetic approaches to cycl (4,3,2) azine

Abstract

1 Synthetic Methods: Three systems of numbering the pyrrocoline ring system hare been employed: The three nameing systems according to this numbering: Pyrrodine(1), Pyrrocoline (11), and Indolizine (111). Throughout this thesis, the name Pyrrocoline adopted by the American Chemical Society will be used. The parent base pyrrocoline was first synthesized by Scholtz, m. Ber 45, 734 (1912) who obtained it by acid hydrolysis of a compound C12H11O2N prepared by the treatment of Picoline with Acetic Anhydride. The new compound was a colourless crystalline solid m.p. 74° b.p. 204°, and steam volatile. The compound had feebly basic properties from which it was not considered to be a true derivative of Pyridine. However, the compound gave with Isatin and with a pine splint, reactions typical of Pyrroles On fusion with oxalic acid the resultant dark melt produced a violet-red colouration in aqueous solution, a reaction typical of Indoles.