Synthesis of 2,3-dimethyl,-1,4-diazacycl[3.2.2]Azine. a novel heteroaromatic system

✍ Scribed by Kazimir Valentin; Alfred Taurins

• Publisher: Elsevier Science
• Year: 1966
• Tongue: French
• Weight: 216 KB
• Volume: 7
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)82839-2

✦ Synopsis

We wish.to report reactions leading to a new heterocyclic system of 1,4-diazacyc1[3.2.2]azine (I). We use the nomenclature proposed by V. Boekelheide in his definitive paper on cyclazines (1). 5-Amino-2-methylimidazo[l,l-alpyridine (2) was acetylated with acetic anhydride. The..reaction mixture was poured on ice and neutralized with ammonium hydroxide. Two products were obtained, the expected acetamide (II) and 5-acetamido-3-acetyl-2-methylimadazo[1,2-alpyridine (III). The solution containing II and III was continuously extracted with ether. From the ether extract yellow needles of III, m.p. 145.5-146.5O, were obtained (0.54 g.: 17% yield). The compound fluoresced yellow in ultraviolet light. Its n.m.r. spectrum consisted of eleven lines (an AMX system with two overlapping lines) in the 7-0 p.p.m. region. There were also three separate bands at 2.25, 2.69 and 2.70 p.p.m., assigned to the methyl groups. The EIi absorption was observed at an unusually low field,,1'2.66 p.p.m.