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Magnetically recoverable copper ferrite catalyzed cascade synthesis of 1,3‐dimethyl‐6‐nitro‐5‐arylpyrido[2,3‐ d ]pyrimidine‐2,4(1 H ,3 H )‐diones under microwave irradiation and solvent‐less condition
Author(s) -
Bhuyan Amar Jyoti,
Bhuyan Pubanita,
Boruah Bornali,
Saikia Lakhinath
Publication year - 2021
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.6091
Subject(s) - chemistry , catalysis , methylene , pyrimidine , cascade reaction , nitro , cycloaddition , yield (engineering) , combinatorial chemistry , medicinal chemistry , organic chemistry , stereochemistry , alkyl , materials science , metallurgy
In recent years, magnetically active CuFe 2 O 4 nanoparticles have been gaining significant interest in the field of heterogeneous catalysis as those can be easily prepared and effortlessly recovered from a reaction system. Here, we are reporting our work on cascade syntheses of 1,3‐dimethyl‐6‐nitro‐5‐arylpyrido[2,3‐ d ]pyrimidine‐2,4(1 H ,3 H )‐diones starting from 6‐[(dimethylamino)methylene‐amino]‐1,3‐dimethyluracil, aromatic aldehydes and nitromethane using magnetically active CuFe 2 O 4 catalyst system under microwave irradiation and solvent‐less condition. The current methodology is a valued addition to the existing procedures of 5‐arylpyrido[2,3‐ d ]pyrimidines syntheses making best use of the diene behavior of 6‐[(dimethylamino)methylene‐amino]‐1,3‐dimethyluracil. However, heterogeneous catalysis has been employed for the first time to do the syntheses by carrying out [4 + 2]cycloaddition reaction between 6‐[(dimethylamino)methylene‐amino]‐1,3‐dimethyluracil and in situ generated 2‐(2‐nitrovinyl)arenes/heteroarenes. The methodology is highly time‐economic, and along with other features like easy recovery and good reusability of the catalyst, simple operating procedure, wide substrate scope, and good to excellent product yield, it offers the chemists a reaction protocol worth trying for the syntheses of 1,3‐dimethyl‐6‐nitro‐5‐arylpyrido[2,3‐ d ]pyrimidine‐2,4(1 H ,3 H )‐diones. While laboratory prepared catalyst system was characterized using FT‐IR, XRD, SEM‐EDX, VSM, XPS and TEM analysis, all the synthesized compounds have been characterized using 1 H and 13 C NMR spectroscopy and HRMS.