Efficient synthesis and free-radical scavenging capacity of new 2,4-substituted tetrahydroquinolines prepared via BiCl3-catalyzed three-component Povarov reaction, using N-vinylamides

被引：0
作者：
Vladimir V. Kouznetsov
Carlos M. Meléndez Gómez
Luz K. Luna Parada
John H. Bermudez
Leonor Y. Vargas Méndez
Amner Muñoz Acevedo
机构：
[1] Universidad Industrial de Santander,Laboratorio de Química Orgánica y Biomolecular, Escuela de Química
[2] Universidad del Atlántico,Grupo de Investigación en Compuestos Heterocíclicos, Programa de Química, Facultad de Ciencias Básicas
[3] Universidad Santo Tomás,Grupo de Investigaciones Ambientales, Facultad de Química Ambiental
[4] Universidad del Norte,Departamento de Química y Biología
来源：
Molecular Diversity | 2011年 / 15卷
关键词：
MCRs; Reaction imino Diels–Alder (Povarov); 2,4-disubstituted tetrahydroquinolines; Structural diversity; DOS methodology; Antioxidant agents;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Efficient synthesis of new structurally different 2-(het)aryl-4-amidyl-substituted tetrahydroquinolines 8–29 is reported. The synthesis based on BiCl3-catalyzed three-component Povarov reaction between anilines, (het)aryl aldehydes and enamides offers a fast, safe, and cheap way for efficient tetrahydroquinoline libraries construction. Using N-vinylamides (N-vinylpyrrolidin-2-one and N-vinylacetamide) in this reaction, it was possible to obtain two series of different cis tetrahydroquinolines with antioxidant properties. Among 14 tested compounds, 7 tetrahydroquinolines revealed a prominent anti-radical capacity, equal or higher than that of the commercial antioxidants. Being the most active molecule, the N-[2-(α-furanyl)-6-methoxy-1,2,3,4-tetrahydroquinolin-4-yl] acetamide 21 was ca. 2.2-fold more potent than the well-known antioxidant, vitamin E (α-tocopherol).
引用
收藏
相关论文
共 124 条
  • [1] Arya P(2005)Exploring new chemical space by stereocontrolled diversity-oriented synthesis Chem Biol 12 163-180
  • [2] Joseph R(2005)Diversity-oriented synthesis exploring the intersections between chemistry and biology Nat Chem Biol 1 74-84
  • [3] Gan Z(2004)Stereoselective diversity-oriented solution and solid-phase synthesis of tetrahydroquinoline-based polycyclic derivatives J Comb Chem 6 54-64
  • [4] Rakic B(2004)Solution- and solid-phase synthesis of natural product-like tetrahydroquinoline-based polycyclics having a medium size ring J Comb Chem 6 735-745
  • [5] Tan DS(2003)Diversity-oriented synthesis; a challenge for synthetic chemists Org Biomol Chem 1 3867-3870
  • [6] Arya P(2008)Diversity-oriented synthesis; a spectrum of approaches and results Org Biomol Chem 6 1149-1158
  • [7] Durieux P(2004)Synthesis of some secondary amine derivatives bearing a heteroaryl fragment J Chil Chem Soc 49 107-203
  • [8] Chen Z-X(2002)Antioxidant activity of aromatic cyclic amine derivatives Polym Degrad Stab 75 549-554
  • [9] Joseph R(2003)Antioxidant activity of the fused heterocyclic compounds, 1,2,3,4-tetahydroquinolines, and related compounds—effect of ortho-substituents Polym Degrad Stab 79 225-230
  • [10] Leek D(2002)The antioxidant ethoxyquin and its analogues: A review Int J Food Properties 5 451-461
12345678910