Singh Priyanka, Kaur Navpreet, Banerjee Prabal
Department of Chemistry, Indian Institute of Technology Ropar, Nangal Road, Rupnagar, Punjab 140001, India.
J Org Chem. 2020 Mar 6;85(5):3393-3406. doi: 10.1021/acs.joc.9b03170. Epub 2020 Feb 4.
A highly regioselective synthesis of tetrahydropyrrolo1,2-]uinazolin-5(1)one derivatives was achieved by reacting cyclopropane aldehydes with '-aryl anthranil hydrazides in the presence of -toluene sulfonic acid (PTSA). The transformation involves domino imine formation and intramolecular cyclization to form 2-arylcyclopropyl-2,3-dihydroquinolin-4(1)-one, followed by nucleophilic ring opening of the cyclopropyl ring to form desired tetrahydropyrrolo[1,2-]quinazolin-5(1)one in good to excellent yield with complete regioselectivity. This protocol tolerates a great variety of functional groups and thus provides a simple and step-efficient method for pyrroloquinazolinone synthesis.
通过在对甲苯磺酸（PTSA）存在下，使环丙烷醛与邻氨基苯甲酰芳基酰肼反应，实现了四氢吡咯并[1,2 - ]喹唑啉 - 5(1)酮衍生物的高度区域选择性合成。该转化过程涉及多米诺亚胺形成和分子内环化，生成2 - 芳基环丙基 - 2,3 - 二氢喹啉 - 4(1) - 酮，随后环丙基环发生亲核开环，以良好至优异的产率和完全的区域选择性形成所需的四氢吡咯并[1,2 - ]喹唑啉 - 5(1)酮。该方法耐受多种官能团，因此为吡咯并喹唑啉酮的合成提供了一种简单且步骤高效的方法。
