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Synthesis, Structure, and Functionalization of Homo Heterocalix[2]arene[2]triazines: Versatile Conformation and Cavity Structures Regulated by the Bridging Elements
Chen, Yin1; Wang, De-Xian1; Huang, Zhi-Tang1; Wang, Mei-Xiang1,2
2010-06-04
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume75Issue:11Pages:3786-3796
AbstractA number of homo[2] and homo[4] heterocalix[2]arene[2]triazines were synthesized through a general and good-yielding fragment coupling approach starting from cyanuric halides, aromatic and aliphatic diols, and diamines under very mild reaction conditions. While homo[2] tetraazacalix[2]arene[2]triazine gave a twisted and pinched 1,2-alternate conformer, almost all homo[2] heterocalix[2]arene[2]triazines adopted different partial cone conformations in the solid state. Homo[41] heterocalix[2]arene[2]triazines yielded more diverse conformational structures including partial cone, pinched partial cone, 1,2-alternate and twisted 1.2-alternate, depending on the nature abridging moieties. On the basis of (1)H NMR spectra, homo[2] and homo[4] heterocalix[2]arene[2]triazines were fluxional macrocycles in solution, and they underwent rapid conformation interconversion at different temperatures. Efficient and straightforward nucleophilic aromatic substitution reaction and palladium-catalyzed cross-coupling reactions on chlorotriazine rings, and the nucleophilic alkylation reaction on the bridging nitrogen atoms led to the construction of various highly functionalized homo heterocalix[2]arene[2]triazine derivatives.
DOI10.1021/jo100571c
Indexed BySCI ; IC
Language英语
WOS IDWOS:000278063100028
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:42[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/70246
Collection中国科学院化学研究所
Corresponding AuthorWang, Mei-Xiang
Affiliation1.Chinese Acad Sci, Beijing Natl Lab Mol Sci, Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
2.Tsinghua Univ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Dept Chem, Beijing 100084, Peoples R China
Recommended Citation
GB/T 7714
Chen, Yin,Wang, De-Xian,Huang, Zhi-Tang,et al. Synthesis, Structure, and Functionalization of Homo Heterocalix[2]arene[2]triazines: Versatile Conformation and Cavity Structures Regulated by the Bridging Elements[J]. JOURNAL OF ORGANIC CHEMISTRY,2010,75(11):3786-3796.
APA Chen, Yin,Wang, De-Xian,Huang, Zhi-Tang,&Wang, Mei-Xiang.(2010).Synthesis, Structure, and Functionalization of Homo Heterocalix[2]arene[2]triazines: Versatile Conformation and Cavity Structures Regulated by the Bridging Elements.JOURNAL OF ORGANIC CHEMISTRY,75(11),3786-3796.
MLA Chen, Yin,et al."Synthesis, Structure, and Functionalization of Homo Heterocalix[2]arene[2]triazines: Versatile Conformation and Cavity Structures Regulated by the Bridging Elements".JOURNAL OF ORGANIC CHEMISTRY 75.11(2010):3786-3796.
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