Preparation and Application of a New Supported Nicotine-Based Organocatalyst for Synthesis of Various 1,5-Benzodiazepine
- PDF / 2,628,569 Bytes
- 10 Pages / 595.276 x 790.866 pts Page_size
- 91 Downloads / 191 Views
Preparation and Application of a New Supported Nicotine-Based Organocatalyst for Synthesis of Various 1,5-Benzodiazepines Mehri Moeini korbekandi1 · Mahboobeh Nasr‑Esfahani1 · Iraj Mohammadpoor‑Baltork1 · Majid Moghadam1 · Shahram Tangestaninejad1 · Valiollah Mirkhani1 Received: 26 June 2018 / Accepted: 8 January 2019 © Springer Science+Business Media, LLC, part of Springer Nature 2019
Abstract A new nicotine-based organocatalyst supported on silica nanoparticles (Fe(III)-NicTC@nSiO2) was prepared and characterized by different techniques. A series of 1,5-benzodiazepines derivatives were smoothly synthesized via the tandem process, starting from o-phenylenediamine and dimedone (or 1,3-cyclohexanedione), followed by addition of aldehyde in the presence Fe(III)-NicTC@nSiO2 catalyst in water at room temperature. The Fe(III)-NicTC@nSiO2 was also applied as an efficient catalyst for the selective synthesis of mono- and bis-1,5-benzodiazepines. Excellent yields and selectivity, short reaction time, mild conditions, and reusability of the catalyst are valuable features of this method. Graphical Abstract A new supported nicotine-based organocatalyst was prepared, characterized and applied for the synthesis of 1,5-benzodiazepines in water at room temperature.
Keywords Organocatalyst · Nicotine · 1,5-Benzodiazepines · Bis-1,5-benzodiazepines · Water media
1 Introduction The design of safe, sustainable, non-polluting materials and processes has attracted the attention of chemical scientists, leading to the growth of green chemistry [1]. The use of Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10562-019-02668-z) contains supplementary material, which is available to authorized users. * Iraj Mohammadpoor‑Baltork [email protected] * Majid Moghadam [email protected] 1
Catalysis Division, Department of Chemistry, University of Isfahan, Isfahan 81746‑73441, Iran
organocatalytic systems for the synthesis of fine chemicals provided a powerful ecofriendly strategy, due to the benefit of organic nature, the air- and water-tolerating reaction conditions and easy set-up [2–5]. However, high loading and trouble separation of organocatalyst has led to a widespread interest in immobilization of them on the surface, bringing simple recovery and reuse of the catalysts [6, 7]. Many organic compounds such as pyridines, alkaloids, amino acids, piperidine and pyrrolidine were immobilized on the solid materials to provide supported organocatalysts. Nevertheless, some of these substances are known as toxic materials [8–11]. Recently, nicotine has been applied as a fragment of some organocatalysts [12, 13]. Although, the backbone of nicotine composed from both pyridine and pyrollidine moieties but the toxicity of nicotine is far less of each of these ingredients.
13
Vol.:(0123456789)
1,5-Benzodiazepines are an imperative class of benzofused seven-membered heterocycles, which show various biological and pharmaceutical activities. These heterocycles have been also used in co
Data Loading...
