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Vitamin B1 as a metal-free organocatalyst for greener Paal–Knorr pyrrole synthesis

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Abstract

This investigation discloses a greener reaction to prepare pyrrole derivatives. Metal-free catalysts are greener alternatives to existing metal catalysts in synthetic organic chemistry. Indeed, transition metals are often costly and toxic. They may be found as traces in health reaction products such as pharmaceuticals. Alternatively small organic molecules termed “organocatalysts” allow the synthesis of valuable products without traces of toxic metals. Here, we show for the first time the use of vitamin B1 as new organocatalyst for the Paal–Knorr pyrrole synthesis under ambient conditions. Reaction conditions were optimized for the reaction of hexane-2,5-dione with 4-methoxyaniline. Ethanol was the most effective solvent. The conversion was quantitative using vitamin B1, by comparison with a low yield of 30 % without catalysis. The best conditions were performed in ethanol with 5 mol % of vitamin B1 during 1 h. This reaction was tested using various aromatic amines. To conclude the use of vitamin B1 for the Paal–Knorr pyrrole, cyclocondensation has mild reaction conditions, is simple to perform, and gives moderate to excellent yields. It is therefore a promising reaction for the preparation of various pyrrole derivatives.

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Authors and Affiliations

  1. Chemistry and Chemical Engineering Research Center of Iran, Pajoohesh Blvd., km 17, Karaj Hwy, Tehran, 14968-13151, Iran

    Hossein Reza Darabi, Kioumars Aghapoor, Abbas Darestani Farahani & Farshid Mohsenzadeh

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  1. Hossein Reza Darabi
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  2. Kioumars Aghapoor
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  3. Abbas Darestani Farahani
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  4. Farshid Mohsenzadeh
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Correspondence to Hossein Reza Darabi.

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Darabi, H.R., Aghapoor, K., Darestani Farahani, A. et al. Vitamin B1 as a metal-free organocatalyst for greener Paal–Knorr pyrrole synthesis. Environ Chem Lett 10, 369–375 (2012). https://doi.org/10.1007/s10311-012-0361-7

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  • DOI: https://doi.org/10.1007/s10311-012-0361-7

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