Synthesis of 2-Oxazoline-2-amines and 2-Thiazoline-2-amines by Reaction of Aziridinium Tetrafluoroborate with Isocyanates and Isothiocyanates

✍ Scribed by Prof. E. Pfeil; K. Milzner

• Publisher: John Wiley and Sons
• Year: 1966
• Tongue: English
• Weight: 118 KB
• Volume: 5
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.196606671

✦ Synopsis

However, many side reactions occur, in contrast to the cyclization of nitrosouracils. When, for instance, a solution of 4-methylamino-5-p-nitrobenzylideneaminouracil(Ia) in nitrobenzene is refluxed for only a short time (2-5 min), fractional crystallization of the product leads to a 40 % yield of 7-p-nitrobenzyltheophylline (2a) and a 12 % yield of 8-p-nitrophenylisocaffeine (3a). Since the Schiff bases (Ib)-(Id) also afford 7-benzyltheophyllines (2b)-(2d) as main products in yields around SO%, the reaction must