Microwave-Assisted, Multicomponent, Ecofriendly Synthesis of 3-Bihetaryl-2-oxindole Derivatives Grafted with Phenothiazine Moiety

Abstract

A series of 3-(3′-pyrrolyl)-2-oxindoles incorporating the phenothiazine moiety has been synthesized under both conventional and microwave heating conditions via multicomponent reaction of 3-(2-(phenothiazin-2-yl)-2-oxoethylidene)-2-oxindole derivatives, acyclic and cyclic 1,3-dicarbonyl compounds, and ammonium acetate. The resulting 2-oxindole derivatives underwent selective chloroacetylation at both the oxindole and the phenothiazine NH groups. Treatment of the dichloroacetylated compound with 2 mol of sodium azide in acetone under reflux gave the corresponding monoazide with concomitant dechloroacetylation of the N-chloroacetyl group of the oxindole ring. Huisgen 1,3-dipolar cycloaddition of the resulted alkyl azide with diethyl acetylene–dicarboxylate afforded the corresponding triazole derivative in good yield. Furthermore, the dichloroacetylated compound could be easily cyclized into 4-(3-oxo-2,3-dihydroxazolo[3,2-a]indol-9-yl)-1H-pyrrole-3-carboxylate derivative by treatment with sodium hydride in dry toluene. The yields and rate of reactions significantly improved under microwave heating conditions.

GRAPHICAL ABSTRACT

Keywords:

• 2,3-Dihydroxazolo[3,2-a]indole
• Michael addition
• microwave
• phenothiazine
• 3-(3′-pyrrolyl)-2-oxindole
• triazole

SUPPLEMENTAL MATERIAL

Full experimental details and ¹H and ¹³C NMR spectra for this article can be accessed on the publisher’s website.