Ce-Zr/SiO2: A versatile reusable heterogeneous catalyst for three ...

Electronic Supplementary Material (ESI) for RSC Advances This journal is © The Royal Society of Chemistry 2013

Ce-Zr/SiO 2 : A versatile reusable heterogeneous catalyst for threecomponent synthesis of 2-amino-4H-pyranoquinoline derivatives Ramakanth Pagadala, Suresh Maddila, Surjyakanta Rana, Sreekantha B. Jonnalagadda* School of Chemistry & Physics, University of KwaZulu-Natal, Westville Campus, Chiltern Hills, Durban-4000, South Africa. *Corresponding author Tel.: +27 31 260 7325/3090; fax: +27 31 260 3091; E-Mail: [email protected]

1% Ce-Zr/SiO2 Adsorption 1% Ce-Zr/SiO2 Desorption

600

Quantity (cm3/g STP)

500 400 300 200 100 0

0.0

0.2

0.4 0.6 Relative Pressure

0.8

1.0

Fig 1. BET surface area and pore size of Ce-Zr/SiO 2

Fig 2. SEM-EDX of Ce-Zr/SiO 2 S1


Apparatus and analysis All chemicals used were reagent grade and were used as received without further purification. 1 H NMR and 13C NMR spectra were recorded at 25 oC at 400 MHz and 100 MHz (Bruker Avance) instrument respectively, using TMS as internal standard. Chemical shifts are given in parts per million (ppm). The FT-IR spectroscopy of samples was carried out on a Perkin Elmer Perkin Elmer Precisely 100 FT-IR spectrometer in the 400-4000 cm-1 region. LCMS mass spectra were recorded on a MASPEC low resolution mass spectrometer operating at 70 eV. Elemental analyses were carried out using a Perkin-Elmer CHNS Elemental Analyzer model 2400. Reactions were monitored and the purity of products was checked out on thin layer chromatography (TLC) on aluminium-backed plates coated with Merck Kieselgel 60 F254 silica gel, visualizing the spots under ultraviolet light and iodine chamber. Melting points are uncorrected and were recorded on a hot stage melting point apparatus Ernst Leitz Wetzlar, Germany.

1

H NMR spectra of compound 4a

S2


15

N NMR (ghsqc) spectra of compound 4a

13

C NMR spectra of compound 4a

S3


FTIR spectra of compound 4a

1

H NMR spectra of compound 4b S4


15

N NMR (ghsqc) spectra of compound 4b

13

C NMR spectra of compound 4b S5


FTIR spectra of compound 4b

1

H NMR spectra of compound 4c S6


15

N NMR (ghsqc) spectra of compound 4c

13

C NMR spectra of compound 4c S7


FTIR spectra of compound 4c

1

H NMR spectra of compound 4d S8


15

N NMR (ghsqc) spectra of compound 4d

13

C NMR spectra of compound 4d S9


FTIR spectra of compound 4d

1

H NMR spectra of compound 4e S10


15

N NMR (ghsqc) spectra of compound 4e

13

C NMR spectra of compound 4e S11


FTIR spectra of compound 4e

S12


1

H NMR spectra of compound 4f

15

N NMR (ghsqc) spectra of compound 4f

13

C NMR spectra of compound 4f S13


FTIR spectra of compound 4f

S14