Teja Chitrala, Babu Spoorthy N, Noor Ayesha, Daniel J Arul, Devi S Asha, Nawaz Khan Fazlur Rahman
Organic and Medicinal Chemistry Research Laboratory, Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology Vellore-632014 Tamil Nadu India
Centre for Bio Separation Technology, Vellore Institute of Technology Vellore-632014 India.
RSC Adv. 2020 Mar 25;10(21):12262-12271. doi: 10.1039/d0ra01553a. eCollection 2020 Mar 24.
A series of spiro-[indoline-3,3'-pyrrolizin/pyrrolidin]-2-ones, 4, 5 and 6 were synthesized in a sequential manner from Cu-TEMPO catalyzed dehydrogenation of alkylated ketones, 1 followed by 1,3-dipolar cycloaddition of azomethine ylides decarboxylative condensation of isatin, 2 and l-proline/sarcosine, 3 in high regioselectivities and yields. The detailed mechanistic studies were performed to identify the reaction intermediates, which revealed that the reaction proceeds dehydrogenative cycloaddition. Additionally, the regio and stereochemistry of the synthesized derivatives were affirmed by 2D NMR spectroscopic studies. The synthesized derivatives were explored further with molecular docking, antioxidant, and anti-diabetic activities.
通过铜-四甲基哌啶氧化物（Cu-TEMPO）催化烷基化酮1脱氢，随后依次进行甲亚胺叶立德的1,3-偶极环加成、异吲哚酮2与L-脯氨酸/肌氨酸3的脱羧缩合反应，以高区域选择性和产率合成了一系列螺[吲哚啉-3,3'-吡咯嗪/吡咯烷]-2-酮4、5和6。进行了详细的机理研究以确定反应中间体，结果表明该反应通过脱氢环加成进行。此外，通过二维核磁共振光谱研究确定了合成衍生物的区域和立体化学。对合成的衍生物进一步进行了分子对接、抗氧化和抗糖尿病活性研究。
