Regioselective synthesis of new 5H,10H-dipyrimido[2,1-b:4′,5′-d][1,3]thiazine: a combined experimental and computational study

被引:4
作者
Afrough, Toktam [1 ]
Bakavoli, Mehdi [1 ]
Eshghi, Hossein [1 ]
Tajabadi, Javad [1 ]
Mague, Joel [2 ]
机构
[1] Ferdowsi Univ Mashhad, Dept Chem, Fac Sci, Mashhad 917751436, Razavi Khorasan, Iran
[2] Tulane Univ, Dept Chem, New Orleans, LA 70118 USA
关键词
Dipyrimido[2; 1-b; 4 '; 5 '-d] [1; 3]thiazine; heterocyclization; regioselectivity; computational calculations; DERIVATIVES; STEEL;
D O I
10.1080/17415993.2019.1576685
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Several derivatives of the novel tricyclic system 'dipyrimido[2,1-b:4 ',5 '-d][1,3]thiazine' were synthesized via inter- and intramolecular heterocyclization of 2,4-dichloro-5-(chloromethyl)-6-methylpyrimidine and 6-amino-4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile in short reaction times under mild conditions. An x-ray analysis together with computational calculations was performed to gain an in-depth understanding of regioselectivity of the reaction. [GRAPHICS] .
引用
收藏
页码:265 / 276
页数:12
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