以4,6-二氯-5-氨基嘧啶为原料,经N-烃基化反应、缩合反应和氯化反应,合成了一系列未见文献报道的6-氯-8-烃基-9-芳基嘌呤衍生物,所有化合物均通过<'1>H NMR、MS和元素分析确定其结构.研究结果表明,N-烃基化反应时,芳胺使用盐酸作催化剂,芳基脂肪胺用有机碱三乙胺作催化剂,缩合反应时,多聚磷酸(PPA)用量过多会影响传质效果,影响反应的收率.讨论了微波反应方式对氯化反应的影响.
参考文献
[1] | Narender P,Suyeal B,Padmanava P.Synthesis and Reactions of 2-Chloro-and 2-Tosyloxy-2-deoxyinosine Derivatives[J].J Org Chem,2005,70:7188-7195. |
[2] | Svjetlana P,Drazenka S,Tatjana G.Synthesis and Biological Evaluation of lodinated and Fluorinated 9-(2-Hydroxypmpyl) and 9-(2-Hydroxyethoxy) methyl Purine Nueleoside Analogues[J].J Med Chem,2003,46:5763-5772. |
[3] | Melissa P,Jiang J,Athena M K."Reversine" and Its 2-Substituted Adenine Derivatives as Potent and Selective A<,3> Adenosine Receptor Antagonists[J].J Med Chem,2005,48:4910-4918. |
[4] | LU Hongfei,HAN Guangfan,LU Ming.Synthesis of 6-Fluorine-subsfituted-purine Derivatives[J].J Org Chem,2008,28(8):1462-1466(in Chinese).陆鸿飞,韩光范,陆明.嘌呤6位含氟基团取代衍生物的合成[J].有机化学,2008,28(8):1462-1466. |
[5] | Szezepankiewicz B G,Rnhde J J,Kurukulasuriya R.Synthesis of Purines and Other Fused Imidazoles from Acyclic Amidines and Guanidines[J].Org Lett,2005,7(9):1833-1835. |
[6] | Iain W,Caroline A,Rupert A.Evaluation of a Series of Bicyclic CXCR2 Antagonists[J].Bioorg Med Chem Lett,2008,18:798-803. |
[7] | Hocek M,Pohl R.Regioselectivity in Cross-Coupling Reactions of 2,6,8-Trichloro-9-(tetrnhydropyran-2-yl) purine:Synthesis of 2,6,8-Trisubstituted Purine Bases[J].Synthesis,2004,17:2869-2876. |
[8] | Kato K,Hayakawa H,Miyasaka T L.Lithiation-mediated C-C Silyl and Stannyl Migrations Observed in 6-Cldoro-9-(β-Dribofuranosyl) purine[J].Tetrahedron Lett,1995,36:6507-6510. |
[9] | Qun D,Brian S B,Mark D E.Effcient Synthesis of Purine Analogues:an FeCl<,3>-SiO<,2>-Promoted Cyclization Reaction of 4,5-Diaminopyrimidines with Aldehydes Leading to 6,8,9-tri-Substituted Purines[J].Tetrahedron Lett,2000,41:6559-6562. |
[10] | Lisa C W C,Ronald F S,Jacobien K.2,6-Disubstituted and 2,6,8-Trisubstituted Purines as Adenosine Receptor Antagonists[J].J Med Chem,2006,49:2861-2867. |
[11] | Marco A B,Jiandong S,Kevin H.Orally Active Purine-Based Inhibitor of the Heat Shock Protein 90[J].J Med Chem,2006,49:817-828. |
[12] | Jianxin Y,Qun D.Preparation of a Fully Substituted Purine Library[J].J Comb Chem,2005,7:474-482. |
[13] | Jinglin L,Qun D.An Efficient and Regiospecific Strategy to N<'7>-Substituted Purines and Its Application to a Library of Trisubstituted Purines[J].J Comb Chem,2006,8:410-416. |
[14] | Nada I,Michel L.ChemInform Abstract:High-Yielding Two-Step Synthesis of 6,8-Disubstituted N-9-Unprotected Purines[J].J Comb Chem,2009,11:658-666. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分:
-
10%
-
20%
-
30%
-
40%
-
50%