A regio and diastereoselective transformation of 3-dienyl-2-azetidinones to novel pyrroloxazine

✍ Scribed by Amit Anand; Gaurav Bhargava; Vipan Kumar; Mohinder P. Mahajan

• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 296 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.02.127

✦ Synopsis

The regioselective nitroso Diels-Alder (NDA) cycloadditions of 3-dienyl-2-azetidinones with nitrosobenzene to generate oxazine-substituted b-lactams in excellent yields are reported. The amidiolytic ring opening of the cycloadducts with sodium methoxide followed by iodocyclization using I 2 /K 2 CO 3 etiquette to capitulate previously unknown, multisubstituted pyrroloxazine in outstanding yields is also accounted.