Polymer-Supported Fe-Phthalocyanine Derived Heterogeneous Photo-Catalyst for the Synthesis of Tetrazoles Under Visible L
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Polymer‑Supported Fe‑Phthalocyanine Derived Heterogeneous Photo‑Catalyst for the Synthesis of Tetrazoles Under Visible Light Irradiation Vijay Baburao Khajone1 · Kamlesh Rudreshwar Balinge2 · Pundlik Rambhau Bhagat1 Received: 27 May 2020 / Accepted: 11 November 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract Herein, a polymer supported Fe-Phthalocyanine entangled with carboxyl functionalized benzimidazolium moiety (PSFePcCFBM) explored as heterogenous photocatalyst, for regioselective synthesis of 1H-tetrazoles from sodium azide and other affordable substrates. The PSFePcCFBM displayed good to excellent yield of the product (79–91%) under visible light (5 W) irradiations using home-made photoreactor. The N aN3 acts as a nitrogen donor of tetrazoles ring as well as it convert aldehyde into isocyanide as one of the nitrogen sources. The catalyst could be recycled up to 5th run successfully without altering its catalytic activity. The small amount of the catalyst loading, extensive substrate range, ease of separation of the catalyst by simple filtration, less reaction time, simple workup procedure, and excellent product yield are the salient features of the investigated protocol. Graphic Abstract
Keywords PSFePcCFBM · Heterogenous photo-catalyst · Visible light (5 W) · 1H-Tetrazoles
1 Introduction Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10562-020-03461-z) contains supplementary material, which is available to authorized users. * Pundlik Rambhau Bhagat [email protected] Extended author information available on the last page of the article
Tetrazoles are the class of heterocyclic compounds with a five-member ring containing four adjacent nitrogen atoms with one carbon atom. Such a heterocyclic system is not existing in nature. Due to characteristic structure and biological activity, tetrazoles are found a wide series of practical
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applications in medicine, chemistry, and material-science [1–4]. From a perspective of pharmaceutical chemistry, tetrazole derivatives exhibited numerous biological activities such as antifungal [5], antibacterial [6], antiviral [7], antiinflammatory [8], anticancer [9] anti-diabetic [10], antiallergic [11], anti-arrhythmic [12] antihypertensive [13] and antibiotics [14]. Moreover, tetrazoles also play an important role in drug development as an inhibitor for human immunodeficiency viruses and other immune diseases [15]. The functional group of tetrazoles has a substantial role as a ligand in the coordination chemistry [16]. Traditional synthesis of tetrazoles has been described to progress via [3 + 2] cycloaddition of azide ions with expensive and toxic nitrile [17]. As compare to nitriles, aldehydes, are highly attractive for the synthesis of tetrazole due to easy accessibility, lower toxicity, and easiness of handling. Green chemistry methods continue to grow in significant alternative routes to conserve resources and reduce costs [18]. In this respect, green
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