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

Mahsa Fathi; M Reza Naimi-Jamal; Mohammad G Dekamin; Leila Panahi; Oleg M Demchuk

doi:10.1038/s41598-021-84209-6

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

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

Authors

Mahsa Fathi¹, M Reza Naimi-Jamal², Mohammad G Dekamin¹, Leila Panahi¹, Oleg M Demchuk³

Affiliations

¹ Research Laboratory of Green Organic Synthesis and Polymers, Department of Chemistry, Iran University of Science and Technology, Tehran, 16846-13114, Islamic Republic of Iran.
² Research Laboratory of Green Organic Synthesis and Polymers, Department of Chemistry, Iran University of Science and Technology, Tehran, 16846-13114, Islamic Republic of Iran. naimi@iust.ac.ir.
³ Pharmaceutical Research Institute, 8 Rydygiera Street, 01-793, Warsaw, Poland.

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 SO₃H functionalized-silica (MCM-41-SO₃H) 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.

Publication types

Research Support, Non-U.S. Gov't