Microwave-assisted expeditious and efficient synthesis of cyclopentene ring-fused tetrahydroquinoline derivatives using three-component Povarov reaction

TETRAHEDRON LETTERS

卷:54

Article

Kulkarni, Abhijit R.¹  Thakur, Ganesh A.^1,2 

[1] Northeastern Univ, Dept Pharmaceut Sci, Bouve Coll Pharm, Boston, MA 02115 USA

[2] Northeastern Univ, Ctr Drug Discovery, Boston, MA 02115 USA

关键词: Tetrahydroquinolines;    Nicotinic Acetylcholine Receptors;    Microwave-assisted synthesis;    Allosteric Modulators;    Povarov reaction;   

DOI  :  10.1016/j.tetlet.2013.09.107

来源: Elsevier

【 摘 要 】

We report here an efficient and expeditious microwave-assisted synthesis of cyclopentadiene ring-fused tetrahydroquinolines using the three-component Povarov reaction catalyzed by indium (III) chloride. This method has an advantage of shorter reaction time (10-15 min) with high and reproducible yields (up to 90%) and is suitable for parallel library synthesis. The optimization process is reported and the results from the microwave route are compared with those of the conventional synthetic route. In almost all cases, the microwave acceleration consistently provided improved yields favoring the cis-diastereomer. (C) 2013 Elsevier Ltd. All rights reserved.

【 授权许可】

Free