Three-Component, One-Pot Sequential Synthesis of Functionalized Cyclazines: 3H‑1,2a1,3-Triazaacenaphthylenes

• Published in: Journal of organic chemistry Vol. 77; no. 23; pp. 10745 - 10751
• Main Authors: Sun, Hongpeng, Zhou, Huayong, Khorev, Oleg, Jiang, Ruwei, Yu, Ting, Wang, Xin, Du, Yongli, Ma, Yi, Meng, Tao, Shen, Jingkang
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 07.12.2012
• Subjects: Acenaphthenes - chemical synthesis; Acenaphthenes - chemistry; Aza Compounds - chemical synthesis; Aza Compounds - chemistry; Catalysis; Chemistry; Combinatorial Chemistry Techniques; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Molecular Structure; Organic chemistry; Preparations and properties; Pyridines - chemistry; Stereoisomerism; One pot reaction; Catalytic reaction; Cyclazine; Imidazopyridine derivatives; Multicomponent reaction; Functionalization; Molecular structure; Nitrogen heterocycle; Ytterbium triflate; Tandem reaction; Chemical synthesis; Successive reaction
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo3021105

An efficient tandem route to the synthesis of 3H-1,2a1,3-triazaacenaphthylene derivatives of the cyclazine family has been developed. Target compounds were obtained in moderate to good yields by a Yb(OTf)3/Ag2CO3-catalyzed, three-component domino reaction. This in turn will set the stage for a wide application of this useful reaction for the synthesis of structurally diverse polyheterocyclic skeletons containing the imidazo[1,2-a]pyridine privileged structure.