Abstract

[Bmim]OH mediated new synthesis of 3-(1 H -Indol-3-Yl)Acrylonitrile derivatives 6 have been developed by the reaction of diethylphthalate 1 with ethyl cyanohydrazide 2 to form 3-(1, 4-dioxo-3, 4-dihydrophthalazin-(1H)-yl)-3-oxopropanenitrile 3. Then compound 3 reacted with indole-3-aldehyde 4 by Knoevenagel condensation to form compound (E)-2-(1, 4-dioxo-1, 2, 3, 4-tetrahydrophthalazine-2-carbonyl)-3-(1H-indol-3-yl)acrylonitriles 5 . Compound 5 under go alkylation with alkylating agents to form 6 with good yields. Compound 6 could also be synthesized by alkylation of 4 followed by condensation with 3.

Highlights

  • Ionic liquids as catalysts1 and /or media2 in reactions have been widely used in organic transformations due to their advantages such as good solvating ability, negligible vapor pressure, high polarity and ease of work-up. [Bmim]OH (1butyl-3-methylimidazolium hydroxide) is one such taskspecified ionic liquid which acts as reaction medium as well as a basic catalyst and has got various applications3 in the field of synthetic methodology development

  • We have developed the condensation of diethyl phthalate (1) (1 mmol), ethyl cyanoacetic acid hydrazide8 (2) (1 mmol) to from 3-(1,4-dioxo-3,4-dihydrophthalazin(1H)-yl)-3-oxopropanenitrile17 (3) in the presence of 1ethyl-3-methylimidazolium hydroxide solution [Bmim]OH (5 ml) at 80 °C for 15-20 min

  • Heterocycles containing the phthalazine moiety are of interest because they show some pharmacological and biological activities

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Summary

Introduction

Ionic liquids as catalysts1 and /or media2 in reactions have been widely used in organic transformations due to their advantages such as good solvating ability, negligible vapor pressure, high polarity and ease of work-up. [Bmim]OH (1butyl-3-methylimidazolium hydroxide) is one such taskspecified ionic liquid which acts as reaction medium as well as a basic catalyst and has got various applications3 in the field of synthetic methodology development. Compound 3 (1 mmol) was reacted with indole-3-aldehyde (4a) (1 mmol) in the presence of [Bmim]OH (5 ml) at 80 °C for 30-35 min to form 2-(1,4-dioxo-1,2,3,4-tetrahydrophthalazine-2-carbonyl)-3-(1H-indol-3-yl)acrylonitriles (5a) in 87 % yield on simple work-up of reaction mixture (TABLE 1, entry 1).

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