Practical and Novel One-Pot Protocol for the Synthesis of Highly Functionalized Pyridinols and Pyrido[1,2-a]-Fused 1,3-Diazaheterocycles

被引:18
作者
Alizadeh, Abdolali [1 ]
Rezvanian, Atieh [1 ]
机构
[1] Tarbiat Modares Univ, Dept Chem, Tehran 18716, Iran
关键词
pyridinol; pyrido[1,2-a]-fused 1,3-diazaheterocycle; Michael addition reaction; 1; n-diamine; nitro ketene dithioacetal; l-bis(methylthio)-2-nitroethene; dibenzylideneacetone; HETEROCYCLIC KETENE AMINALS; DIELS-ALDER REACTIONS; CYCLOCONDENSATION REACTIONS; FUSED DIAZAHETEROCYCLES; SUBSTITUTED PYRIDINES; ETHYL BROMOACETATE; CARBONYL COMPOUNDS; FACILE SYNTHESIS; ALKYLATION; CHLORIDE;
D O I
10.1055/s-0030-1259942
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and efficient protocol for the generation of substituted pyridinols and pyrido[1,2-a]-fused 1,3-diazaheterocycles from primary amine or 1, n-diamine, nitro ketene dithioacetal [1, l-bis(methylthio)-2-nitroethene] and dibenzylideneacetone as starting materials in a one-pot process combining a Michael addition reaction and nucleophilic addition under mild condition in high yield has been developed.
引用
收藏
页码:1105 / 1108
页数:4
相关论文
共 58 条
[1]   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
[2]   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
[3]   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
[4]   Synthesis of pyrimido[6,1-a]isoquinolines via a one-pot, four-component reaction [J].
Alizadeh, Abdolali ;
Rezvanian, Atieh ;
Zhu, Log-Guan .
TETRAHEDRON, 2010, 66 (34) :6924-6927
[5]  
Balasubramanian M., 1996, COMPREHENSIVE HETERO, V5, P245, DOI 10.1016/B978-008096518-5.00109
[6]   The role of natural product chemistry in drug discovery [J].
Butler, MS .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (12) :2141-2153
[7]  
CHAFER H, 1977, J PRAKT CHEM, P87
[8]  
Cook A.G., 1988, Enamines: synthesis, structure, and reactivity
[9]   1,1-BIS(METHYLTHIO)-2-NITROETHENE IN SUPERACIDS - NMR-STUDY AND REACTIVITY OF THE FORMED HYDROXYNITRILIUM ION [J].
COUSTARD, JM .
TETRAHEDRON, 1995, 51 (40) :10929-10940
[10]  
COUSTARD JM, 1996, TETRAHEDRON, V51, P9509