N-aryl-substituted anthranilamides with intramolecular hydrogen bonds

doi:10.1016/j.tet.2014.09.057

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	N-aryl-substituted anthranilamides with intramolecular hydrogen bonds
	Wang, Li-Xia 1; Hu, Ben-Quan 1,3; Xiang, Jun-Feng 2; Cui, Jie 2; Hao, Xiang 2; Liang, Tong-Ling 2; Tang, Ya-Lin 1,2
刊名	TETRAHEDRON
	2014-11-11
卷号	70 期号:45 页码:8588-8591
关键词	Nmr Spectroscopy N-aryl-substituted Anthranilamides Intramolecular Hydrogen Bonds Chemical Shifts Crystal Structure
ISSN号	0040-4020
DOI	10.1016/j.tet.2014.09.057
英文摘要	Hydrogen bonding interaction as one type of non-covalent force has proven itself to be highly efficient for constructing structurally unique artificial secondary structures. Here, the structure of N-aryl-substituted anthranilamide in solution is demonstrated by various NMR technique, the intramolecular hydrogen bonds between amide attached to arylamine of the same ring is proposed, which is supported by its crystal structure in the solid phase. The substituent on the nitrogen atom of arylamine plays an important role in forming the presence of intramolecular hydrogen bonds. The chemical shift of the N-aryl-H downfield changes obviously, due to the formation of intramolecular hydrogen bonds and the deshielding effect of oxygen, and the neighboring C-H is activated and shows downfield protonic signal too. The presence of intramolecular hydrogen bonds probably provides the explanation for the transformation from N-aryl-substituted anthranilamide to imine, which could be converted into 2-aryl quinazolinone finally. (C) 2014 Elsevier Ltd. All rights reserved.
语种	英语
出版者	PERGAMON-ELSEVIER SCIENCE LTD
WOS记录号	WOS:000345815100019
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/50731]
专题	中国科学院化学研究所
通讯作者	Xiang, Jun-Feng
作者单位	1.Chinese Acad Sci ICCAS, Inst Chem, State Key Lab Struct Chem Unstable & Stable Speci, Beijing 100190, Peoples R China 2.Chinese Acad Sci ICCAS, Inst Chem, Ctr Physcochem Anal & Measurement, Beijing 100190, Peoples R China 3.Xiangtan Univ, Dept Chem, Key Lab Environm Friendly Chem & Applicat, Xiangtan 411105, Hunan, Peoples R China
推荐引用方式 GB/T 7714	Wang, Li-Xia,Hu, Ben-Quan,Xiang, Jun-Feng,et al. N-aryl-substituted anthranilamides with intramolecular hydrogen bonds[J]. TETRAHEDRON,2014,70(45):8588-8591.
APA	Wang, Li-Xia.,Hu, Ben-Quan.,Xiang, Jun-Feng.,Cui, Jie.,Hao, Xiang.,...&Tang, Ya-Lin.(2014).N-aryl-substituted anthranilamides with intramolecular hydrogen bonds.TETRAHEDRON,70(45),8588-8591.
MLA	Wang, Li-Xia,et al."N-aryl-substituted anthranilamides with intramolecular hydrogen bonds".TETRAHEDRON 70.45(2014):8588-8591.