A simple heterogeneous catalytic process has been established for the single-step synthesis of fused benzoxazinones, quinazolinones, and thiadazines through Markownikoff's hydroamination followed by ...intramolecular cyclization using Cuβ zeolite. The probability and limitations of this catalytic approach were explored using various substrates. The efficiency and feasibility of scaling up the current catalytic system were demonstrated through gram-scale experiments. Moreover, the catalyst was reused for up to five cycles with no noticeable decrease in its catalytic effectiveness. Furthermore, the synthesized compounds were subjected to in vitro assessment to determine their potential as anticancer agents against human cervical epithelioid carcinoma (HeLa), mouse breast cancer (4T-1), and human lung adenocarcinoma (A-549) cell lines. Cytotoxicity studies revealed that 3f, 3b′, 3d′, and 3g′ compounds exhibit anti-cancer activity against breast, cervical and lung cancer cells. Additionally, their antimicrobial activity against bacteria and yeast was also evaluated. The compound 3i exhibited superior antifungal activity against Candida albicans.
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•Cuβ zeolite shows good catalytic activity for synthesis of N-heterocyclic moieties.•Potentiality of this method is ensured with various substrates in good yields.•This approach benefits industrial applications by gram scale experiments.•The catalyst was successfully reused for up to five cycles.•The obtained products were found to be biologically active.
We investigated direct addition reaction of beta-diketone with several alcohols and alkenes employing solid acid zeolites (HY & Hbeta). The presence of acidic sites and the porous structures exhibits ...and influences the catalytic activity. These heterogeneous catalysts were used directly for the nucleophilic addition/substitution reactions. HY zeolite was utilized for the reaction of various aromatic alcohols containing substituents like electron-donating groups, halogens, diphenyl alcohols, propargylic alcohols with acetyl acetone and gave the respective products in 14-99% yields. Hbeta zeolite was used for the reaction of several substituted alkenes with acetyl acetone and afforded their corresponding products from 35 to 98% yields. The validation of large-scale experiments (10 mmol) adds additional dividend to this protocol. Moreover, these heterogeneous zeolites were readily separated from the reaction mixture by simple filtration process. The efficiency of these zeolites (HY and Hbeta) for recyclability was proved for five cycles.
We investigated direct addition reaction of β-diketone with several alcohols and alkenes employing solid acid zeolites (HY & Hβ). The presence of acidic sites and the porous structures exhibits and ...influences the catalytic activity. These heterogeneous catalysts were used directly for the nucleophilic addition/substitution reactions. HY zeolite was utilized for the reaction of various aromatic alcohols containing substituents like electron-donating groups, halogens, diphenyl alcohols, propargylic alcohols with acetyl acetone and gave the respective products in 14–99% yields. Hβ zeolite was used for the reaction of several substituted alkenes with acetyl acetone and afforded their corresponding products from 35 to 98% yields. The validation of large-scale experiments (10 mmol) adds additional dividend to this protocol. Moreover, these heterogeneous zeolites were readily separated from the reaction mixture by simple filtration process
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The efficiency of these zeolites (HY and Hβ) for recyclability was proved for five cycles.
Graphical Abstract
An effective and novel heterogeneous beta zeolite supported CuO (Cuβ) catalyzed double hydroamination of alkynes for the synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones has been achieved in a ...solvent‐free condition. Cuβ zeolite was synthesized by impregnation method. The synthesized Cuβ was characterized by X‐ray diffraction, Fourier transformation infrared spectroscopy, transmission electron microscopy, scanning electron microscopy, and X‐ray photoelectron spectroscopy. Pure Hβ (18 % yield) or Nano CuO (44 % yield) displayed poor catalytic activity, whereas 1 % Cuβ (96 % yield) showed higher catalytic activity for double hydroamination of alkynes due to the synergistic effect of CuO and Hβ zeolite in the reaction. The new protocol offers an appealing approach to a number of di‐substituted quinazolinones with decent to excellent yields. The catalyst has been successfully recycled for up to 5 consecutive cycles.
An efficient heterogeneous 1 % Cuβ zeolite catalyzed double hydroamination of terminal alkynes for the synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones is achieved in a solvent‐free environment. This method offers an appealing approach to a number of di‐substituted quinazolinones with decent to excellent yields.
A wide range of quinazolin-4(3H)-ones have been synthesized from readily accessible precursors such as anthranilamide and 1,3-diketones. This reaction was promoted by the heterogeneous beta zeolite ...as the catalyst via a selective cleavage of the C–C bond of 1,3-diketones. This reaction went smoothly with various 1,3-diketones (cyclic and acyclic) affording 2-aryl and 2-alkyl substituted quinazolin-4(3H)-ones in good to excellent yields. The notable point of this strategy is that it can avoid the involvement of toxic transition metals, additives and corrosive oxidants establishing this method as green and feasible. Besides, this method displays its capacity for gram-scale reactions (up to 10 g). Moreover, in this process the recyclability of the recovered catalyst without drastic changes until 5 cycles have been presented.
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•Hβ zeolite depicted good catalytic activity for synthesis of 2-methylquinazolin-4(3H)-ones.•Potentiality of this method is conferred with different cyclic and acyclic 1,3-diketones.•This process is green and developed without any immobilizations or additives.•This is sustainable and first solvent-free protocol with heterogeneous catalyst.•Mainly, this approach presents synthetic utility by gram scale experiments.
![HY and H[beta] Zeolites Med...](http://api.summon.serialssolutions.com/2.0.0/image/issn/XR4PS5YY4K/1011-372X/small "HY and H[beta] Zeolites Mediated C-C Bond Formation via Addition/Substitution Reaction of 1,3-Dicarbonyl Compounds to Alcohols and Alkenes")
