Multicomponent Domino Process for the Synthesis of Some Novel Benzo[a]chromenophenazine Fused Ring Systems Using H₂SO₄, Phosphotungstic Acid, and [NMP]H₂PO₄

Abstract

Efficient, mild, and quantitative procedures for the synthesis of functionalized benzo[c]chromeno[2,3-a]phenazine derivatives by one-pot, four-component condensation of 2-hydroxynaphthalene-1,4-dione, 1,2-phenylenediamines, aromatic aldehydes, and cyclic 1,3-dicarbonyl compounds have been developed using catalytic amounts of H₂SO₄ and phosphotungstic acid in EtOH/H₂O (1:1) under reflux and also with [NMP]H₂PO₄, which acts as catalyst and medium at 80 °C. The reaction avoids tedious workup procedure due to the direct precipitation of products from the reaction medium. The present finding provides promising synthetic strategies for the synthesis of libraries with functional group diversity.

GRAPHICAL ABSTRACT

Keywords:

• [NMP]H₂PO₄
• 1,2-phenylenediamine
• benzo[a]chromeno phenazine
• cyclic-1,3-dicarbonyl
• H₂SO₄
• phosphotungstic acid

SUPPLEMENTARY DATA

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