Fe₃O₄@SiO₂@propyl‐ANDSA: A new catalyst for the synthesis of tetrazoloquinazolines

Abstract

In this paper, a mild and green protocol has been developed for the synthesis of quinazoline derivatives. The catalytic activity of 7‐aminonaphthalene‐1,3‐disulfonic acid‐functionalized magnetic Fe3O4 nanoparticles (Fe3O4@SiO2@Propyl–ANDSA) was investigated in the one‐pot synthesis of new derivatives of tetrahydrotetrazolo[1,5‐a]quinazolines and tetrahydrobenzo[h]tetrazolo[5,1‐b]quinazolines from the reaction of aldehydes, 5‐aminotetrazole, and dimedone or 6‐methoxy‐3,4‐dihyronaphtalen‐1(2H)‐one at 100 °C in H2O/EtOH as the solvent. The catalyst was characterized before and after the organic reaction. Fe3O4@SiO2@Propyl–ANDSA showed remarkable advantages in comparison with previous methods. Advantages of the method presented here include easy purification, reusability of the catalyst, green and mild procedure, and synthesis of new derivatives in high yields within short reaction time.

Synthesis of bioactive magnetic nanoparticles spiro[indoline‐3,4′‐[1,3]dithiine]@Ni (NO3)2 supported on Fe3O4@SiO2@CPS as reusable nanocatalyst for the synthesis of functionalized 3,4‐dihydro‐2H‐pyran

“…There are a large number of reports on the applications of magnetic nanoparticles (MNPs) in industry and chemistry . Fe 3 O 4 coated as a magnet core and supported by organic compounds has found a special place in the synthesis of heterogeneous magnetic nanocatalysts as such many relevant studies have been carried out in this regard . In addition, Fe 3 O 4 supported and coated can create complexes with different metals and synthesized magnetic organometallic nanocatalysts .…”

Concise Pyrimido[4,5‐d]pyrimidine Synthesis via Direct Annulation of N‐Uracil Amidines with Benzaldehydes Under Transition Metal Free Conditions

“…Recently, pyrimido[4,5‐ d ]pyrimidine analogues of folic acid have also been screened for antitumor activity . Despite their enormous applications, there are only a few methods reported for the synthesis of this class of compounds . Generally, such a goal can be realized by the three‐component reactions involving 6‐aminouracils, or by the cycloaddition reactions between 6‐methylideneaminouracils and electron‐deficient substrates such as N ‐sulfonylimines and imine N ‐oxides (Scheme ).…”

“…Tummaluru and co‐workers have reported the synthesis of pyrimido[4,5‐ d ]pyrimidine derivatives via one‐pot three‐component reaction involving 6‐amino‐ N , N ‐dimethyluracil, phenylisocyanate, and aromatic aldehydes in water solvent . In another approach, Ghorbani‐Vaghei and Sarmast utilized a magnetic nanoparticle Fe 3 O 4 @SiO 2 as catalyst in water solvent for the synthesis of substituted pyrimido[4,5‐ d ]pyrimidines . Recently, Deb and co‐workers have reported a green synthesis of pyrimido[4,5‐ d ]pyrimidine derivatives via a cascade 3‐component reaction involving 6‐aminouracil, aldehyde and tetrahydroisoquinolines under oxidant/catalyst/ solvent free reaction conditions .…”

Butane‐1‐sulfonic acid immobilized on magnetic Fe3O4@SiO2 nanoparticles: A novel and heterogeneous catalyst for the one‐pot synthesis of barbituric acid and pyrano[2,3‐d] pyrimidine derivatives in aqueous media

“…In recent years the use of magnetic nanoparticles (MNPs) for the preparation of supported heterogeneous catalysts has attracted significant attention . This attention can be attributed to the unique properties of these types of compounds including high thermal and mechanical stability, large surface area to volume ratio, low toxicity, ease of recovery by use of an external magnetic field and well‐defined pore size distribution .…”