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

Autor:	Najar AH; Department of Chemistry, Qaemshahr Branch, Islamic Azad University, ‎Qaemshahr, Iran., Hossaini Z; Department of Chemistry, Qaemshahr Branch, Islamic Azad University, ‎Qaemshahr, Iran., Abdolmohammadi S; Department of Chemistry, East Tehran Branch, Islamic Azad University, Tehran, Iran., Zareyee D; Department of Chemistry, Qaemshahr Branch, Islamic Azad University, ‎Qaemshahr, Iran.
Jazyk:	angličtina
Zdroj:	Combinatorial chemistry & high throughput screening [Comb Chem High Throughput Screen] 2020; Vol. 23 (4), pp. 345-355.
DOI:	10.2174/1386207323666200219124625
Abstrakt:	Aims and 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 at ambient temperature under solvent-free conditions and produced α-amino nitriles benzofuran derivatives in high yields. These synthesized compounds may have antioxidant ability. Materials and Methods: ZnO-NRs in these reactions were prepared according to reported article. 2,4-dihydroxyacetophenone 1 (2 mmol) and isopropenylacetylene 2 (2 mmol) were 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 the mixture and stirred for 15 min. After completion of the reaction, as indicated by TLC, isocyanides 5 was added 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 did not have 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 advantages 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. (Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.)
Databáze:	MEDLINE
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