E3S Web of Conferences.
EDP Sciences.
Vol. 159.
2020.
Metal-Free Decarboxylative A3-Coupling/Pictet–Spengler Cascade Accessing Polycyclic Scaffolds: Propiolic Acids Exceed Alkynes
Herein, we describe the development of a metal-free decarboxylative A3-coupling and Pictet–Spengler cascade process to directly generate functionalized tetrahydroisoquinolines from a 2-phenylethanamine, formaldehyde, and a propiolic acid. The key feature of this efficient reactivity is the utilization of a propiolic acid as the alkyne source, with TFA as promoter. This transformation was also demonstrated to be amenable to the construction of N-propargyl thienotetrahydropyridine and benzodiazepine skeletons under mild conditions. © 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Authors
Hu Y.1
,
Shen Y.1
,
Huang L.1
,
Van Der Eycken E.V. ,
Feng H.1
Number of issue
11
Language
English
Pages
1695-1699
Status
Published
Link
Volume
2020
Year
2020
Organizations
- 1 College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai, 201620, China
- 2 Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven, 3001, Belgium
- 3 Department of Chemistry, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, Moscow, 117198, Russian Federation
Keywords
A3-coupling; Decarboxylative coupling; Metal-free; Pictet–Spengler reaction; Tetrahydropyridine
Date of creation
02.11.2020
Date of change
02.11.2020
Share
Other records
ACM International Conference Proceeding Series.
Association for Computing Machinery.
2020.