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通过纳米有序可重复使用催化剂介导的直链、环保的螺[二茚并[1,2-b:2',1'-e]吡啶-11,3'-吲哚啉]-2',10,12-三酮的合成。

A straightforward, environmentally beneficial synthesis of spiro[diindeno[1,2-b:2',1'-e]pyridine-11,3'-indoline]-2',10,12-triones mediated by a nano-ordered reusable catalyst.

机构信息

Research Laboratory of Green Organic Synthesis and Polymers, Department of Chemistry, Iran University of Science and Technology, Tehran, 16846-13114, Islamic Republic of Iran.

Pharmaceutical Research Institute, 8 Rydygiera Street, 01-793, Warsaw, Poland.

出版信息

Sci Rep. 2021 Mar 1;11(1):4820. doi: 10.1038/s41598-021-84209-6.

DOI:10.1038/s41598-021-84209-6
PMID:33649384
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7921678/
Abstract

A library of new spiro[diindeno[1,2-b:2',1'-e]pyridine-11,3'-indoline]-2',10,12-trione derivatives has been prepared in an efficient, one-pot pseudo four-component method mediated by a reusable heterogeneous nano-ordered mesoporous SOH functionalized-silica (MCM-41-SOH) catalyst. Excellent yields, short reaction times, as well as convenient non-chromatographic purification of the products and environmental benefits such as green and metal-free conditions constitute the main advantages of the developed synthetic methodology. The obtained fused indole-indenone dyes would be of interest to pharmaceutical and medicinal chemistry. Furthermore, due to their sensitivity to pH changes, they could be used as novel pH indicators.

摘要

已通过可重复使用的非均相纳米有序介孔 SOH 功能化硅(MCM-41-SOH)催化剂,以高效、一锅法准四级反应,制备了新型螺[二茚并[1,2-b:2',1'-e]吡啶-11,3'-吲哚啉]-2',10,12-三酮衍生物库。该合成方法的主要优点包括:高产率、短反应时间、产品无需色谱纯化、环境友好(绿色、无金属)。所得到的稠合吲哚-茚满二酮染料可能对药物和药物化学具有重要意义。此外,由于它们对 pH 值变化敏感,因此可作为新型 pH 指示剂。

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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a96c/7921678/b6f1d04be7be/41598_2021_84209_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a96c/7921678/bfdb746b9ccb/41598_2021_84209_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a96c/7921678/fe6d768d2011/41598_2021_84209_Fig2_HTML.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a96c/7921678/0294fc2ce088/41598_2021_84209_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a96c/7921678/1f381770f6a2/41598_2021_84209_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a96c/7921678/652f6725494f/41598_2021_84209_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a96c/7921678/f8a40eab3d17/41598_2021_84209_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a96c/7921678/cc4436adad62/41598_2021_84209_Fig8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a96c/7921678/d6c3d8c9a8ff/41598_2021_84209_Sch3_HTML.jpg

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