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

作者：Anand Amit; Bhargava Gaurav; Kumar Vipan; Mahajan Mohinder P^*

来源：Tetrahedron Letters, 2010, 51(17): 2312-2315.

DOI：10.1016/j.tetlet.2010.02.127

• 3-Dienyl-2-azetidinones
• Nitrosobenzene
• 1,2-Oxazines
• Pyrroloxazines

The regioselective nitroso Diels-Alder (NDA) cycloadditions of 3-dienyl-2-azetidinones with nitrosobenzene to generate oxazine-substituted beta-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.