Asef Hajipour Najar, Zinatossadat Hossaini*, Shahrzad Abdolmohammadi and Daryoush Zareyee Pages 1 - 10 ( 10 )
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.
Strecker reaction, antioxidant ability, α–amino nitrile benzofurans, five component reaction, DPPH radical scavenging, ZnO nanorod.
Department of Chemistry, Qaemshahr Branch, Islamic Azad University, Qaemshahr, Department of Chemistry, Qaemshahr Branch, Islamic Azad University, Qaemshahr, Department of Chemistry, East Tehran Branch, Islamic Azad University, Tehran, Department of Chemistry, Qaemshahr Branch, Islamic Azad University, Qaemshahr