Alkali metal cations control over nucleophilic substitutions on aromatic fused pyrimidine-2,4-[1H,3H]-diones: towards new PNA monomers
文献类型：期刊论文
| 作者 | Li, Pengfa1,2; Zhan, Chuanlang1; Zhang, Shanlin1; Ding, Xunlei3; Guo, Fengqi2; He, Shenggui3; Yao, Jiannian1 |
| 刊名 | TETRAHEDRON
 |
| 出版日期 | 2012-10-28 |
| 卷号 | 68期号:43页码:8908-8915 |
| 关键词 | Nucleophilic Substitution Alkali Metal Cation Pna Monomer Solvent Effect Aromatic Fused Pyrimidine-2 4(3h 7h)-diones |
| ISSN号 | 0040-4020 |
| DOI | 10.1016/j.tet.2012.08.028 |
| 英文摘要 | In this paper we report synthesis of a series of aromatic fused pyrimidine-2,4(3H)-dione-1-yl acetic acid and new PNA monomers containing these polycyclic nucleobase analogues. Introduction of a fused aromatic ring onto the 5,6-positions of the pyrimidine-2,4-[1H,3H]-diones brings about the steric effects and the charge delocalization, both weakening the nucleophilic substitutions on the 1- and 3-positions. We found that alkali metal cations play an important role in this alkylation reaction. LiOH brings out a much more efficient alkylation than NaOH does, while KOH nearly does not work on this reaction. Such influences from the alkali metal cations are probably due to that the charge-pairing interactions between the pyrimidine-2,4-dioxide anions and the alkali metal cations rearrange the charge distribution around the whole aromatic system and increase the negative charge distribution on the 1- and 3-nitrogen atoms, which then strengthens the nucleophilic reactivity on these positions. (C) 2012 Elsevier Ltd. All rights reserved. |
| 语种 | 英语 |
| WOS记录号 | WOS:000309252200011 |
| 出版者 | PERGAMON-ELSEVIER SCIENCE LTD |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/49907]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Zhan, Chuanlang |
| 作者单位 | 1.Chinese Acad Sci, Inst Chem, Lab Photochem, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China 2.Zhengzhou Univ, Dept Chem, Zhengzhou 450001, Henan Province, Peoples R China 3.Chinese Acad Sci, Inst Chem, State Key Lab Struct Chem Unstable & Stable Speci, Beijing Natl Lab Mol Sci, Beijing 100080, Peoples R China |
| 推荐引用方式 GB/T 7714 | Li, Pengfa,Zhan, Chuanlang,Zhang, Shanlin,et al. Alkali metal cations control over nucleophilic substitutions on aromatic fused pyrimidine-2,4-[1H,3H]-diones: towards new PNA monomers[J]. TETRAHEDRON,2012,68(43):8908-8915. |
| APA | Li, Pengfa.,Zhan, Chuanlang.,Zhang, Shanlin.,Ding, Xunlei.,Guo, Fengqi.,...&Yao, Jiannian.(2012).Alkali metal cations control over nucleophilic substitutions on aromatic fused pyrimidine-2,4-[1H,3H]-diones: towards new PNA monomers.TETRAHEDRON,68(43),8908-8915. |
| MLA | Li, Pengfa,et al."Alkali metal cations control over nucleophilic substitutions on aromatic fused pyrimidine-2,4-[1H,3H]-diones: towards new PNA monomers".TETRAHEDRON 68.43(2012):8908-8915. |
入库方式： OAI收割
来源：化学研究所
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