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双功能石墨相氮化碳催化剂在水介质中可持续合成3,3-螺环氧化吲哚的位点特异性作用

Site-specific role of bifunctional graphitic carbon nitride catalyst for the sustainable synthesis of 3,3-spirocyclic oxindoles in aqueous media.

作者信息

Dandia Anshu, Mahawar Dinesh Kumar, Saini Pratibha, Saini Surendra, Gupta Shyam L, Rathore Kuldeep S, Parewa Vijay

机构信息

Centre of Advanced Studies, Department of Chemistry, University of Rajasthan Jaipur India

Government Polytechnic College Near Itarana Fly Over, Kalimori Alwar Rajasthan 301001 India.

出版信息

RSC Adv. 2021 Aug 23;11(46):28452-28465. doi: 10.1039/d1ra03881h.

Abstract

Functionalized graphitic carbon nitride (Sg-CN) has been manufactured and used as a reusable catalyst for the one-pot production of various spiro-pyrano chromenes and spiro indole-3,1'-naphthalene tetracyclic systems in aqueous media. An ultrasound-assisted method has been used for the functionalization of g-CN. The catalytic functionalities and the structural integrity of the catalyst were characterized different analytical tools. The catalytic site-specific role of Sg-CN was confirmed various control experiments in one-pot reaction sequences. We recognized that Sg-CN acts as a bifunctional acid-base catalyst for the first reaction sequence whereas it is an acidic catalyst for the second reaction sequence during the one-pot production of various spiro-pyrano chromenes. In addition, the bifunctional acid-base catalytic role of Sg-CN has been confirmed for the first reaction sequence whereas it has a basic catalytic role for the second reaction sequence during the one-pot production of spiro indole-3,1'-naphthalene tetracyclic systems. Diverse C-C, C-O, and C-N bonds, six-membered cycles, stereogenic centers, and spiro frameworks were formed in a single reaction, enhancing the biocidal profile and possibly resulting in the discovery of new medicinal properties. The mild reaction environment, simple workup, easy separation, low cost, heterogeneity, and recyclability of Sg-CN are some rewards of this approach.

摘要

功能化石墨相氮化碳(Sg-CN)已被制备出来,并用作可重复使用的催化剂,用于在水介质中一锅法制备各种螺吡喃色烯和螺吲哚-3,1'-萘四环体系。采用超声辅助方法对g-CN进行功能化。用不同的分析工具对催化剂的催化功能和结构完整性进行了表征。通过一锅反应序列中的各种对照实验证实了Sg-CN的催化位点特异性作用。我们认识到,在各种螺吡喃色烯的一锅法制备过程中,Sg-CN在第一个反应序列中作为双功能酸碱催化剂,而在第二个反应序列中作为酸性催化剂。此外,在螺吲哚-3,1'-萘四环体系的一锅法制备过程中,已证实Sg-CN在第一个反应序列中具有双功能酸碱催化作用,而在第二个反应序列中具有碱性催化作用。在单一反应中形成了多种C-C、C-O和C-N键、六元环、立体中心和螺骨架,增强了杀菌性能,并可能带来新的药用特性的发现。Sg-CN反应环境温和、后处理简单、分离容易、成本低、具有非均相性和可回收性,是这种方法的一些优点。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f139/9038049/aa140ea98b6e/d1ra03881h-f1.jpg

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