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Silica Bonded N-(Propylcarbamoyl)sulfamic acid (SBPCSA) Mediated Expeditious Approach to C–C Bond Formation: An Innovative Pathway for Acrylonitrile Derivatives

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Abstract

A new silica bonded N-(propylcarbamoyl)sulfamic acid (SBPCSA) catalyst has been prepared for the highly efficient synthesis of a series of acrylonitrile derivatives via solvent-free facile Knoevenagel condensation between differently substituted heterocyclic/aromatic aldehydes 1 (a–o) and 2-thiopheneacetonitrile (2). The catalyst was characterized by FT-IR, SEM-EDX and XRD techniques. The thermal stability of the catalyst was evaluated with TGA and DT analysis. The remarkable features of the present protocol are solvent free synthesis, recyclability of the catalyst, mild reaction conditions, shorter reaction profile, excellent yield of products with applicability to broader substrate scope (electron rich and electron deficient) and exclusive formation of E-isomer of the product. DFT calculations also revealed that E-isomer of compound 3f is stabilized by 12.53 kcal mol−1 more than the Z-isomer.

Graphical Abstract

Efficient and economical synthesis of acrylonitrile derivatives.

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Acknowledgments

Shaista Azaz, thanks the Chairman, Department of Chemistry, AMU, Aligarh, for providing the necessary research facilities, University Sophisticated Instrumentation Facility (USIF), AMU, Aligarh and Sophisticated Analytical Instrumentation Facility (SAIF), Chandigarh, is credited for spectral analysis. UGC is also gratefully acknowledged for research fellowship to S. Azaz and F. Ahmad.

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Authors and Affiliations

  1. Division of Organic Synthesis, Aligarh Muslim University, Aligarh, 202002, India

    Mehtab Parveen, Shaista Azaz, Faheem Ahmad & Ali Mohammed Malla

  2. Division of Bioscience, Dongguk University, Gyeongju, 780-714, Republic of Korea

    Mahboob Alam

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  1. Mehtab Parveen
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  2. Shaista Azaz
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  3. Faheem Ahmad
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  4. Ali Mohammed Malla
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  5. Mahboob Alam
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Correspondence to Mehtab Parveen.

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Parveen, M., Azaz, S., Ahmad, F. et al. Silica Bonded N-(Propylcarbamoyl)sulfamic acid (SBPCSA) Mediated Expeditious Approach to C–C Bond Formation: An Innovative Pathway for Acrylonitrile Derivatives. Catal Lett 146, 1687–1705 (2016). https://doi.org/10.1007/s10562-016-1793-7

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