Abstarct: Tetrahydrobenzo[b]pyrans have several biological properties. So, providing a new methodology and synthesis of new derivatives are of interest. In this project, two methods were used for the synthesis of these compounds. Method 1: firstly [SiO2-Caff]HSO4 as a novel heterogeneouse catalyst was prepared; Then, the synthesis of 2-amino-4H-tetrahydrobenzo[b]pyran was catalyzed by [SiO2-Caff]HSO4 at 100oC under solvent-free conditions. Method 2: Three component reaction of 1,3-dicarbonyl compounds with aldehydes and malononitrile in magnetized water at room temperature afforded 2-amino-4H-tetrahydrobenzo[b]pyran. The advantages of this two methods consist of using water as a green solvent, high yield, short reaction time and recycablity of the catalyst.