Synthesis of indeno-[1,2- b]-quinoline-9,11(6 H,10 H)-dione and 7,7-dimethyl-10-aryl-7,8-dihydro-5 H-indeno[1,2- b]quinoline-9,11(6 H,10 H)-dione derivatives in presence of heterogeneous Cu/zeolite-Y as a catalyst

Shankar D Dhengale; Chandrashekhar V Rode; Govind B Kolekar; Prashant V Anbhule

doi:10.1039/d1ra06637d

Synthesis of indeno-[1,2- b]-quinoline-9,11(6 H,10 H)-dione and 7,7-dimethyl-10-aryl-7,8-dihydro-5 H-indeno[1,2- b]quinoline-9,11(6 H,10 H)-dione derivatives in presence of heterogeneous Cu/zeolite-Y as a catalyst

RSC Adv. 2022 Jan 13;12(4):2083-2093. doi: 10.1039/d1ra06637d. eCollection 2022 Jan 12.

Authors

Shankar D Dhengale^{1

2}, Chandrashekhar V Rode², Govind B Kolekar³, Prashant V Anbhule¹

Affiliations

¹ Medicinal Chemistry Research Laboratory, Department of Chemistry, Shivaji University Kolhapur-416004 India pvanbhule@gmail.com.
² Chemical Engineering and Process Development Division, CSIR-National Chemical Laboratory Dr Homi Bhabha Road Pune-411008 India.
³ Fluorescence Spectroscopy Research Laboratory, Department of Chemistry, Shivaji University Kolhapur-416004 MS India.

Abstract

A simple method for the synthesis of indeno-[1,2-b]-quinoline-9,11-(6H,10H)-dione derivatives and 7,7-dimethyl-10-aryl-7,8-dihydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-diones through the reaction of aromatic aldehydes, indan-1,3-dione, dimedone, and p-toluidine/ammonium acetate in the presence of heterogeneous CuO supported on a zeolite-Y catalyst has been investigated in ethanol under reflux conditions. By this method, the reaction time has been reduced, giving an excellent yield of the product. The catalyst was prepared by a hydrothermal method followed by a wet impregnation method. The catalyst had shown Brønsted acid sites and Lewis acid sites. The used catalyst could be actively recycled with a marginal decrease in yield up to five recycles. The prepared catalyst was characterized by FT-IR, pyridine FT-IR, XRD, SEM, EDS, XPS, TEM, and BET surface area analysis. The synthesized compounds were characterized by FT-IR, ¹H NMR, ¹³C NMR and GC-MS spectroscopy.