Fe3O4@SiO2-BenzIm-Fc[Cl]/ZnCl2: a novel and efficient nano-catalyst for the one-pot three-component synthesis of pyran annulated bis-heterocyclic scaffolds under ultrasound irradiation

• Published in: Research on chemical intermediates 2019-04, Vol.45 (4), p.1841-1862
• Main Authors: Gholamhosseini-Nazari, Mahdi, Esmati, Somayeh, Safa, Kazem D., Khataee, Alireza, Teimuri-Mofrad, Reza
• Format: Article
• Language: English
• Subjects: Aldehydes; Catalysis; Catalysts; Catalytic activity; Chemical synthesis; Chemistry; Chemistry and Materials Science; Condensation; Derivatives; Dispersions; Fourier transforms; Infrared spectroscopy; Inorganic Chemistry; Iron oxides; Irradiation; Malononitrile; Organic chemistry; Physical Chemistry; Silicon dioxide; Ultrasonic imaging; Ultrasonic methods; Ultrasonic testing; Zinc chloride
• ISSN: 0922-6168; 1568-5675
• DOI: 10.1007/s11164-018-3704-6

In this study, a novel magnetically recoverable Fe 3 O 4 @SiO 2 -BenzIm-Fc[Cl]/ZnCl 2 nano-particle was synthesized using a simple chemical coprecipitation approach. In the FT-IR spectroscopy of nano-particles, related absorption peaks appeared which confirmed the successful synthesis of nano-catalyst. In the EDX spectrum of the nano-catalyst, the expected elements on their regions appeared. The XRD diffusion patterns of nano-catalysts showed the crystalline dispersions of Fe 3 O 4 magnetic nano-particles. According to the FE-SEM and TEM images, the nano-particles have relative mono-dispersity and the average size of nano-particles is around 35 nm. The catalytic activities of the novel magnetic nano-particle were evaluated in the one-pot three-component synthesis of a wide variety of pyran annulated bis-heterocyclic derivatives (38 compounds) under ultrasonic irradiation. A simple, facial and highly efficient ultrasound-assisted method has been introduced for the synthesis of fused bis-heterocyclic pyran derivatives by one-pot, three-component reactions at room temperature. A series of pyrano[3,2- c ]chromene derivatives were synthesized using a novel nano-catalyst via the condensation reaction of different aldehydes, malononitrile and 4-hydroxycoumarin. Kojic acid was also used in the three-component reaction for the synthesis of pyrano[3,2- b ]pyran derivatives. The method was successful in the synthesis of various pyrano[2,3- d ]pyrimidine derivatives. Additionally, new ultrasound-assisted synthesis protocol was used for the synthesis of novel chromeno[2,3- d ]pyrimidine derivatives via three-component condensation of aromatic aldehydes, orcinol and barbituric acid. The new catalytic method exhibits some notable advantages such as short reaction times, operational simplicity, green reaction conditions, high yields and easy work-up and purification steps. In addition, the novel magnetic nano-particle could be easily separated by an external magnet and reused for six times without significant loss of its catalytic activity in the reaction.