A Novel and Efficient Synthesis of Pyrido[1,2-a]-Fused 1,3-Diazaheterocyclic Compounds via a One-Pot Three-Component Reaction

被引:7
作者
Alizadeh, Abdolali [1 ]
Rezvanian, Atieh [1 ]
机构
[1] Tarbiat Modares Univ, Dept Chem, Tehran, Iran
关键词
Diamines; Ketene dithioacetals; nitro-; Itaconic anhydride; Pyrido[1; 2-a]-fused compounds; Multicomponent reactions;
D O I
10.1002/hlca.201100274
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient one-pot synthesis of pyrido[1,2-a]-fused 1,3-diazaheterocyclic compounds by three-component reaction of diamine, nitroketene dithioacetal (=1,1-bis(methylsulfanyl)-2-nitroethene), and electron-poor itaconic anhydride (=2-methylidenesuccinic anhydride=2-methylidenebutanedioic anhydride) in aqueous EtOH is reported. This protocol has the advantages of easiness, higher yields, and shorter reaction times. The structures were corroborated spectroscopically (IR, 1H- and 13C-NMR, and EI-MS) and by elemental analyses. A plausible mechanism for this type of cyclization is proposed (Scheme 2).
引用
收藏
页码:152 / 156
页数:5
相关论文
共 4 条
[1]   Practical and Novel One-Pot Protocol for the Synthesis of Highly Functionalized Pyridinols and Pyrido[1,2-a]-Fused 1,3-Diazaheterocycles [J].
Alizadeh, Abdolali ;
Rezvanian, Atieh .
SYNLETT, 2011, (08) :1105-1108
[2]   A Novel and One-Pot Multicomponent Approach to the Synthesis of Dihyroindeno[1,2-b]pyrroles and Indeno[2′,1′:4,5]pyrrolo[1,2-a]-Fused 1,3-Diazaheterocycles [J].
Alizadeh, Abdolali ;
Zarei, Ameneh ;
Rezvanian, Atieh .
SYNTHESIS-STUTTGART, 2011, (03) :497-501
[3]   Efficient One-Pot Synthesis of Spirooxindole Derivatives Containing 1,4-Dihydropyridine-Fused-1,3-Diazaheterocycle Fragments via Four-Component Reaction [J].
Alizadeh, Abdolali ;
Firuzyar, Tahereh ;
Mikaeili, Azadeh .
SYNTHESIS-STUTTGART, 2010, (22) :3913-3917
[4]   Novel heterocyclic β-nitroenamines-based on a one-pot three-component reaction: a facile synthesis of fully substituted 1H-pyrrolo[1,2-a]-fused-1,3-diazaheterocycles [J].
Alizadeh, Abdolali ;
Rezvanian, Atieh ;
Deng, Yuan .
TETRAHEDRON, 2010, 66 (52) :9933-9937