School of Chemical Engineering, Yeungnam University, Gyeongsan 38541, Republic of Korea.
J Org Chem. 2020 Dec 4;85(23):15129-15138. doi: 10.1021/acs.joc.0c01991. Epub 2020 Nov 4.
An efficient and facile protocol for the synthesis of biologically and pharmaceutically important phthalimides is developed by l-proline-catalyzed reaction between two dienophiles of α,β-unsaturated aldehydes and maleimides. The reaction involves an efficient benzannulation that proceeds via a formal [4 + 2] cycloaddition of azadiene intermediates generated in situ from enals and N-substituted maleimides. This protocol provides a variety of functionalized phthalimide derivatives, including a potent COX-2 enzyme inhibitor.
脯氨酸催化α,β-不饱和醛和马来酰亚胺的两种亲二烯体之间的反应，开发出一种高效、简便的生物和药物重要的邻苯二甲酰亚胺的合成方法。该反应涉及有效的苯并环化，通过醛和 N-取代马来酰亚胺原位生成的氮杂二烯中间体的形式[4+2]环加成进行。该方案提供了多种功能化的邻苯二甲酰亚胺衍生物，包括一种有效的 COX-2 酶抑制剂。
