Beilstein J. Org. Chem.2023,19, 991–997, doi:10.3762/bjoc.19.74
Elena Y. Mendogralo Maxim G. Uchuskin Perm State University, Bukireva st. 15, Perm, 614990, Russian Federation 10.3762/bjoc.19.74 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.
Keywords: acid hydrolysis; 1,4-diketone; tetrahydrofuro[3,2-c]pyridines; Paal–Knorr reaction; Pictet–Spengler reaction; Introduction
Hydrogenated furo[3,2-c
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Graphical Abstract
Figure 1:
Examples of natural and bioactive hydrogenated furo[3,2-c]pyridines.