N-Alkylation of benzimidazoles with ketonic Mannich bases and the reduction of the resulting 1-(3-oxopropyl)benzimidazoles

被引:6
作者
Roman, Gheorghe [1 ]
机构
[1] Petru Poni Inst Macromol Chem, Iasi 700487, Romania
来源
CENTRAL EUROPEAN JOURNAL OF CHEMISTRY | 2012年 / 10卷 / 05期
关键词
Benzimidazole; Mannich bases; N-alkylation; Reduction; DERIVATIVES; REACTIVITY; CHEMISTRY;
D O I
10.2478/s11532-012-0062-x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Benzimidazole, benzimidazoles diversely substituted at position 2, and 5,6-dimethylbenzimidazole have been alkylated at N (1) with ketonic Mannich bases derived from acetophenones, acetylnaphthalenes, 2-acetylthiophene and 1-tetralone to afford a series of novel 1-(3-oxopropyl)benzimidazoles. The reduction of these transamination products with NaBH4 in methanol produced the corresponding 1-(3-hydroxypropyl)benzimidazoles in excellent yields.
引用
收藏
页码:1516 / 1526
页数:11
相关论文
共 34 条
[21]  
Ramaiah K, 1999, J INDIAN CHEM SOC, V76, P140
[22]   Synthesis and reactivity of Mannich bases. Part 15: Synthesis of 3-(2-(1-pyrazolyl)ethyl)-1,2-benzisoxazoles [J].
Roman, G ;
Comanita, E ;
Comanita, B .
TETRAHEDRON, 2002, 58 (08) :1617-1622
[23]  
Roman G, 2002, KHIM GETEROTSIKL+, P1228
[24]  
Roman G, 2005, COMPT REND ACAD BULG, V58, P397
[25]  
Roman G, 2012, REV CHIM-BUCHAREST, V63, P255
[26]  
Sielemann D, 1999, J PRAK CHEM-CHEM ZTG, V341, P487, DOI 10.1002/(SICI)1521-3897(199907)341:5<487::AID-PRAC487>3.3.CO
[27]  
2-A
[28]   SOME KETONIC MANNICH BASES [J].
TAYLOR, ED ;
NOBLES, WL .
JOURNAL OF THE AMERICAN PHARMACEUTICAL ASSOCIATION, 1960, 49 (05) :317-319
[29]  
TRAMONTI.M, 1973, SYNTHESIS-STUTTGART, P703
[30]   FURTHER ADVANCES IN THE CHEMISTRY OF MANNICH-BASES [J].
TRAMONTINI, M ;
ANGIOLINI, L .
TETRAHEDRON, 1990, 46 (06) :1791-1837