Introduction of a new bis-derivative of succinimide (Bis-Su) as a sustainable and efficient basic organo-catalyst for th
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Introduction of a new bis‑derivative of succinimide (Bis‑Su) as a sustainable and efficient basic organo‑catalyst for the synthesis of arylidene malononitrile and tetrahydrobenzo[b]pyran derivatives under green conditions Fariba Hassanzadeh1 · Nader Daneshvar1 · Farhad Shirini1,2 · Manouchehr Mamaghani1,2 Received: 11 April 2020 / Accepted: 6 August 2020 © Springer Nature B.V. 2020
Abstract Organo-catalysts have been under great consideration for many years because of their performance and selectivity in the reactions. In this work, a new bis-succinimide (Bis-Su) compound is prepared, identified and used as a green and efficient basic organo-catalyst for the promotion of the synthesis of arylidene malononitrile and tetrahydrobenzo[b]pyran derivatives. Using this method, both of the reactions were performed under mild conditions, during short reaction times in high yields. The catalyst can also be recycled and reused several times without a considerable decrease in its activity. Keywords Organo-catalyst · Bis-succinimide · Arylidene malononitriles · Tetrahydrobenzo[b]pyran · Water media
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1116 4-020-04235-3) contains supplementary material, which is available to authorized users. * Farhad Shirini [email protected] Nader Daneshvar [email protected] 1
Department of Chemistry, College of Science, University of Guilan, University Campus 2, Rasht, Iran
2
Department of Chemistry, College of Sciences, University of Guilan, Rasht, Iran
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Introduction In recent years, the use of green and commercially available or easily preparable catalysts in organic reactions has been under attention because they do not contaminate the environment and are economically affordable. In this way, organo-catalysts as compounds that have the only hydrogen, carbon, nitrogen, sulfur and phosphor atoms in their structure have been extensively followed up since they are usually, inexpensive, easily available, non-toxic and non-sensitive toward moisture and oxidation. Also, these compounds can be utilized in various conversions with excellent selectivity and yields. Besides, organo-catalysts are free of metals, making them an environmentally friendly and valuable portion of green chemistry [1–4]. Succinimide is a cyclic imide which can be easily prepared from the reaction of succinic acid with ammonia in the presence of some catalysts. It can also be prepared by the thermal decomposition of ammonium succinate [5]. Some of its derivatives such as N-chlorosuccinimide (NCS) [6], N-bromosuccinimide (NBS) [7] and N-sulfonated succinimide are very important because that they show promoting effect in special organic transformations [8]. Despite its derivatives, there is not any report about the promoting catalytic activity of succinimide on its own. Arylidene malononitrile compounds are important chemical intermediates that can be obtained via reactions between different types of aldehydes and mal
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