ZnO-nanorods Promoted Synthesis of α-amino Nitrile Benzofuran Derivatives using One-pot Multicomponent Reaction of Isocyanides

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Author(s): Asef Hajipour Najar, Zinatossadat Hossaini*, Shahrzad Abdolmohammadi, Daryoush Zareyee.

Journal Name: Combinatorial Chemistry & High Throughput Screening
Accelerated Technologies for Biotechnology, Bioassays, Medicinal Chemistry and Natural Products Research

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Aims & Objective: In this work ZnO-nanorod (ZnO-NR) as reusable catalyst promoted Strecker-type reaction of 2,4-dihydroxyacetophenone, isopropenylacetylene, trimethylsilyl cyanide (TMSCN), primary amines and isocyanides carried out at ambient temperature under solvent-free conditions and produced α-amino nitriles benzofuran derivatives in high yields. These synthesized compounds maybe have antioxidant ability.

Materials and Methods: ZnO-NRs in these reactions were prepared according to reaported article.

2,4-dihydroxyacetophenone 1 (2 mmol) and isopropenylacetylene 2 (2 mmol) was mixed and stirred for 30 min in the presence of ZnO-NR (10 mol%) under solvent-free conditions at room temperature. After 30 min primary amine 3 (2 mmol) was added to the mixture gently and the mixture was stirred for 15 min. After this time TMSCN 4 (2 mmol) was added to mixture and stirred for 15 min. After completion of the reaction, as indicated by TLC, isocyanides 5 add to mixture in the presence of catalyst.

Results: In the first step of this research, the reaction of 2,4-dihydroxyacetophenone 1, isopropenylacetylene 2, methyl amine 3a, trimethylsilyle cyanide 4 and tert-butyl isocyanides 5a was used as a sample reaction to attain the best reaction conditions. The results showed this reaction performed with catalyst and haven’t any product without catalyst after 12 h.

Conclusion: In conclusion, we investigate multicomponent reaction of 2,4-dihydroxyacetophenone 1, isopropenylacetylene 2, primary amines 3, trimethylsilyl cyanide 4 and isocyanides along with ZnO-NRs as reusable catalyst at room temperature under solvent-free conditions which generates α-amino nitrile benzofuran derivatives in high yields. The chief benefits of our method are high atom economy, green reaction conditions, higher yield, shorter reaction times, and easy work-up, which are in good agreement with some principles of green chemistry. The compounds 8c exhibit excellent DPPH radical scavenging activity and FRAP compared to synthetic antioxidants BHT and TBHQ.

Keywords: Strecker reaction, antioxidant ability, α–amino nitrile benzofurans, five component reaction, DPPH radical scavenging, ZnO nanorod.

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(E-pub Ahead of Print)
DOI: 10.2174/1386207323666200219124625
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