PTSA-Catalyzed Cyclization of 6-Aminouracils with Diimines: Efficient Synthesis of Functionalized Tetrahydropyrimido[4,5-d]pyrimidine-2,4-diones

被引：8

作者：

Khodabakhshi, Mohammad R. ^{[1
]}

Kiamehr, Mostafa ^{[2
]}

Moghaddam, Firouz M. ^{[3
]}

Villinger, Alexander ^{[4
]}

Langer, Peter ^{[4
,5
]}

机构：

[1] Baqiyatallah Univ Med Sci, Appl Biotechnol Res Ctr, Vanak Sq,Mollasadra Ave,POB 1435915371, Tehran, Iran

[2] Univ Qom, Fac Sci, Dept Chem, Ghadir Blvd,POB 3716146611, Qom, Iran

[3] Sharif Univ Technol, Dept Chem, Lab Organ Synth & Nat Prod, POB 11155-9516, Tehran, Iran

[4] Univ Rostock, Inst Chem, Albert Einstein Str 3a, D-18059 Rostock, Germany

[5] Univ Rostock, Leibniz Inst Katalyse eV, Albert Einstein Str 29a, D-18059 Rostock, Germany

来源：

CHEMISTRYSELECT | 2018年 / 3卷 / 41期

关键词：

aminouracil; cyclization; heterocycles; nucleobases; pyrimidines; GROWTH-FACTOR RECEPTOR; BIGINELLI DIHYDROPYRIMIDINE SYNTHESIS; TYROSINE KINASE INHIBITORS; DIELS-ALDER REACTION; ONE-POT SYNTHESIS; ANTIINFLAMMATORY ACTIVITY; DIHYDROFOLATE-REDUCTASE; THYMIDYLATE SYNTHASE; POTENTIAL INHIBITORS; IN-VITRO;

D O I：

10.1002/slct.201801869

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new and efficient method has been developed for the synthesis of 5,7-diaryl-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidine-2,4-dione derivatives by cyclization of 6-aminouracils with N,N '-bis(arylmethylidene)arylmethanes (diimines). The products were formed in good yields and with very good anti-diastereoselectivity. The best yields were obtained when p-toluenesulfonic acid (PTSA) was used as the catalyst. The solvent also played an important role in the optimization. An amino-substituted 6-aminouracil and a corresponding sulfur analog could be successfully employed. In addition, various diimines, electron rich and neutral, could be successfully employed. The products are of relevance as analogs of biologically active drugs and natural products.

引用

页码：11671 / 11676

页数：6

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