Synthesis of tetrahydrofuro[3,2-c]pyridines via Pictet – Spengler reaction

Abstract
A semi-one-pot method for the synthesis of 4-substituted tetrahydrofuro[3,2-c]pyridines by the Pictet–Spengler reaction was developed. The method is based on the condensation of easily accessibly 2-(5-methylfuran-2-yl)ethanamine with commercially available aromatic aldehydes followed by acid-catalyzed Pictet–Spengler cyclization. Using this approach, we synthesized a range of 4-substituted tetrahydrofuro[3,2-c]pyridines in reasonable yields. The reactivity of some of the products was investigated and selected synthetic transformations of the obtained tetrahydrofuro[3,2-c]pyridines were shown.

Beilstein J. Org. Chem. 2023, 19, 991–997. doi:10.3762/bjoc.19.74

Source: Beilstein Journal of Organic Chemistry - June 30, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: acid hydrolysis 1,4-diketone tetrahydrofuro[3,2-c]pyridines Paal – Knorr reaction Pictet Spengler reaction Full Research Paper Source Type: research