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

Content Provider	Europe PMC
Author	Mendogralo, Elena Y Uchuskin, Maxim G
Editor	Baxendale, Ian
Copyright Year	2023
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.
Volume Number	19
PubMed Central reference number	PMC10315887
PubMed reference number	37404803
Journal	Beilstein Journal of Organic Chemistry [Beilstein J Org Chem]
e-ISSN	18605397
DOI	10.3762/bjoc.19.74
Language	English
Publisher	Beilstein-Institut
Publisher Date	2023-06-30
Publisher Place	Germany
Access Restriction	Open
Rights License	This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material. Copyright © 2023, Mendogralo and Uchuskin
Subject Keyword	acid hydrolysis 1,4-diketone tetrahydrofuro[3,2-c]pyridines Paal–Knorr reaction Pictet–Spengler reaction
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry