An efficient diastereoselective synthesis of novel fused 5H-furo[2,3-d]thiazolo[3,2-a]pyrimidin-5-ones via one-pot three-component reaction

被引:7
作者
Tabibi, Tooba [1 ]
Esmaeili, Abbas Ali [1 ]
Mague, Joel T. [2 ]
机构
[1] Ferdowsi Univ Mashhad, Dept Chem, Fac Sci, Mashhad, Razavi Khorasan, Iran
[2] Tulane Univ, Dept Chem, New Orleans, LA 70118 USA
关键词
7-benzoyl-6-(aryl)-6,7-dihydro-5H-furo[2,3-d]thiazolo[3,2-a]pyrimidin-5-one; Phenacyl bromide; Isoquinoline; Thiazolo[3,2-a]pyrimidin; Three-component reaction; N-PHENACYLBENZOTHIAZOLIUM BROMIDES; BIOLOGICAL EVALUATION; CYCLOADDITION REACTION; 1,3-DIPOLAR CYCLOADDITION; DERIVATIVES; YLIDES; ANALOGS; INDOLIZINES; METHYLIDES; CASCADE;
D O I
10.1007/s11030-020-10173-4
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Herein, a convenient and efficient synthesis of 7-benzoyl-6-(aryl)-6,7-dihydro-5H-furo[2,3-d]thiazolo[3,2-a]pyrimidin-5-one derivatives was achieved from the reaction of isoquinolinium N-ylides, aromatic aldehydes, and heterocyclic 1,3-dicarbonyl compounds via one-pot three-component diastereoselective domino reaction in good-to-excellent yields. The advantages of this protocol are easily available starting materials, operational simplicity, and avoidance of hazardous organic solvents and catalyst. The synthesized products were characterized by IR, H-1 NMR, C-13 NMR and mass spectra. Additionally, the conclusive structure of target compounds was confirmed by X-Ray diffraction analysis. [GRAPHICS] .
引用
收藏
页码:183 / 190
页数:8
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