Nano-ZnO Catalyzed Multicomponent One-Pot Synthesis of Novel Spiro(indoline-pyranodioxine) Derivatives

Abstract

A simple catalytic protocol for the synthesis of novel spiro[indoline-pyranodioxine] derivatives has been developed using ZnO nanoparticle as an efficient, green, and reusable catalyst. The derivatives are obtained in moderate to excellent yield by one-pot three-component reaction of an isatin, malononitrile/ethylcyanoacetate, and 2,2-dimethyl-1,3-dioxane-4,6-dione in absolute ethanol under conventional heating and microwave irradiation. The catalyst was recovered by filtration from the reaction mixture and reused during five consecutive runs without any apparent loss of activity for the same reaction. The mild reaction conditions and recyclability of the catalyst make it environmentally benign synthetic procedure.

Zinc‐Catalysed Multi‐Component Reactions: An Overview

“…A methodology for the synthesis of spiro (indoline‐pyranodioxine) compounds using zinc oxide NPs as catalyst was reported . 2,2‐Dimethyl‐1,3‐dioxane‐4,6‐dione (meldrum's acid), ethylcyanoacetate/dicyanomethane, and indoline 2,3‐dione were subjected to two types of reaction conditions‐ one utilising microwave heating while the other using traditional method of heating (Scheme ).…”

“…A nano zinc oxide‐catalysed strategy towards pyranopyrazole synthesis was reported in which methylacetocetate, ethylcyanoacetate, hydrazine hydrate and aromatic aldehydes reacted utilising 9 mol % nano ZnO in water at 25 °C for 55–60 min. affording the pyranopyrazoles in good yields ( Scheme ) . Nano ZnO catalysed the reaction by providing the Lewis base and acid sites for the product formation.…”

Comparative study of the cytotoxic properties of isatin-containing derivatives of 4-thiazolidinone with different structure toward human tumor cells in vitro

“…Відома велика кількість синтетичних гетероциклічних сполук [7], частину з яких широко використовують у сучасній медицині. Їхніми основними перевагами над сполуками природного походження є нижча вартість виробництва і широкі можли-вості хімічної модифікації з метою підвищення біологічної активності.…”

H3PW12O40@nano‐ZnO: An efficient, recyclable, and eco‐friendly catalyst for the green synthesis of novel benzo[a]pyrimido[5′,4′:5,6]pyrano[2,3‐c]phenazines via sequential multicomponent reactions under microwave irradiation

“…Consequently, the design of novel MCRs using microwave irradiation (MWI) and nanocatalysts for the synthesis of simple and complex bioactive heterocycles has remained a notable topic in the drug discovery process and the analysis of drugs . Among them, functionalized nitrogen and oxygen heterocycles are of interest because of their potential medicinal and biological activity …”