One‐pot, Three‐component Synthesis of a New Series of 2‐Amino‐4‐aroyl‐5‐oxo‐5,6‐dihydro‐2H‐pyrano[3,2‐c]quinoline‐3‐carbonitrile in the Presence of SBA‐15 as a Nanocatalyst

Abstract

One‐pot, three‐component reaction of arylglyoxals, malononitrile and 4‐hydroxyquinolin‐2(1H)‐one in the presence of SBA‐15 as a nanocatalyst and using green solvent systems under various temperatures afforded the 2‐amino‐4‐aroyl‐5‐oxo‐5,6‐dihydro‐2H‐pyrano[3,2‐c]quinoline‐3‐carbonitrile derivatives. The best yield (70‐96%) were obtained using 20% mol of SBA‐15 as a nanocatalyst in H2O/EtOH (1:1) at 80 °C. The simplicity of work up procedure, using green solvent system, and good to excellent yields of products are the main advantages of this synthetic strategy.

One‐pot, Three‐component Synthesis of a Series of New Bis‐pyrrolo[2,3‐d]pyrimidines in the Presence of TPAB under Reflux Conditions

“…In attempting to develop a facile one‐pot, three‐component reaction for synthesis of pyrrolo[2,3‐ d ]pyrimidine derivatives, we have previously reported the synthesis of pyrrolo[2,3‐ d ]pyrimidine derivatives starting from aryl glyoxals .…”

“…The barbituric acid, thiobarbituric acid, and 6‐aminouracil moieties have a wide range of applications in medicinal chemistry owing to their biological and pharmacological activities . There are many reports on synthesis of pyrido, pyrimido, and pyrrolopyrimidine derivatives with biological and pharmaceutical applications such as antimicrobial , anti‐inflammatory , anticancer , analgesic , anticonvulsants , antiviral , inhibitor of replication of a hepatitis C virus (HCV) , anesthesia , and HIV‐1 inhibitor .…”

Synthesis and Reactions of the Novel 6‐ethyl‐4‐hydroxy‐2,5‐dioxo‐5,6‐dihydro‐2H‐pyrano[3,2‐c]quinoline‐3‐carboxaldehyde

“…Infrared spectra were recorded on FT-IR Bruker Vector 22 spectrophotometer using KBr wafer technique. 1 H NMR (500 MHz) and 13 C NMR (125 MHz) spectra were measured on Bruker apparatus, using DMSO-d 6 as a solvent and tetramethylsilane (δ) as the internal standard. Mass spectra were obtained using GC-2010 Shimadzu Gas chromatography instrument mass spectrometer (70 eV).…”

“…The reactivity of aldehyde 2 was examined toward some active methylene nitrile, namely, malononitrile, ethyl cyanoacetate, and cyanoacetamide leading to 2-iminopyrano[2 0 ,3 0 :4,5]pyrano[3,2-c] quinolines 10-12, respectively. Also, some novel pyrazolo[4″,3″:5 0 ,6 0 ]pyrano[2 0 ,3 0 :4,5]pyrano[3,2-c]quinolines (13,14) and thiazolo[5″,4″:5 0 ,6 0 ]pyrano[2 0 ,3 0 :4,5]pyrano[3,2-c]quinolines (15, 16) were synthesized. Structures of the new synthesized products were deduced on the basis of their analytical and spectral data.…”

One‐pot, three‐component synthesis of polyfunctionalized benzo[h]pyrazolo[3,4‐b][1,6]naphthyridine and benzo[g]pyrazolo[3,4‐b]quinoline derivatives in the presence of silver nanoparticles (AgNPs)

“…In continuation of our previous studies on the application of aryl glyoxals in the synthesis of heterocyclic compounds, [ 22–29 ] herein, we report a one‐pot, three‐component reaction of aryl glyoxal monohydrates, 5‐amino‐1‐aryl‐3‐methylpyrazoles, and 4‐hydroxyquinoline‐2(1 H )‐one or 2‐hydroxy‐1,4‐naphthoquinone (lawsone) using AgNPs as nanocatalyst in H 2 O/EtOH under mild conditions to afford the corresponding pyrazolonaphthyridines and pyrazoloquinolines, respectively, in good to high yields.…”