Compared with the well-developed cyclization of functionalized propargylamines, the use of unactivated tertiary propargylamines to access pyrroles remains challenging. Herein, we report an efficient method for constructing tetrasubstituted pyrroles via a DBU-mediated intramolecular cycloaddition of -alkyl propargylamines. This reaction employs cyclization to access dihydropyrrole intermediates, followed by oxidation to produce pyrroles in the presence of 2,3-dichloro-5,6-dicyano--benzoquinone. In addition, a broad substrate scope, high atom economy, high selectivity, and simple operation are also advantages of this protocol.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.joc.4c02198 | DOI Listing |
J Org Chem
March 2025
College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620, China.
Compared with the well-developed cyclization of functionalized propargylamines, the use of unactivated tertiary propargylamines to access pyrroles remains challenging. Herein, we report an efficient method for constructing tetrasubstituted pyrroles via a DBU-mediated intramolecular cycloaddition of -alkyl propargylamines. This reaction employs cyclization to access dihydropyrrole intermediates, followed by oxidation to produce pyrroles in the presence of 2,3-dichloro-5,6-dicyano--benzoquinone.
View Article and Find Full Text PDFChem Asian J
March 2025
Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur Botanic Garden, Howrah, 711103, India.
Herein, we describe a sustainable Co(II)-catalyzed synthesis of pyrroles and pyridines. Using a Co(II)-catalyst [Co (L)Cl] (1 a) bearing redox-active 2-(phenyldiazenyl)-1,10-phenanthroline) (L) scaffold, various substituted pyrroles and pyridines were synthesized in good yields, taking alcohol as one of the primary feedstock. Pyrroles were synthesized by the equimolar reaction of 2-amino and secondary alcohols.
View Article and Find Full Text PDFOrg Biomol Chem
December 2024
Department of Chemistry, Birla Institute of Technology and Science, Pilani 333031, Rajasthan, India.
Construction of a chiral methanamine unit at the C3 position of pyrrole is highly desirable; nevertheless, it remains challenging due to its intrinsic electronic properties. Herein, we present an operationally straightforward and direct asymmetric approach for accessing α-(3-pyrrolyl)methanamines under benign organocatalytic conditions for the first time. The one-pot transformation proceeds smoothly through an amine-catalyzed direct Mannich reaction of succinaldehyde with various -cyclic imines, followed by a Paal-Knorr cyclization with a primary amine.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Laboratory of Synthesis and Natural Products I, nstitute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
We report in this paper a novel Cu-catalyzed synthesis of polysubstituted 1-pyrrolines. The reaction of β,γ-unsaturated oxime esters 4 with terminal alkynes 5 in the presence of a catalytic amount of Cu(OAc) and 2,2'-biquinoline affords the corresponding 1,6-enynimines, which undergo a highly stereoselective Alder-ene reaction to afford 1-pyrrolines with concomitant generation of a quaternary carbon and a 2-azadiene motif. It represents an unusual [4+1] heteroannulation reaction wherein terminal alkynes act as a one carbon donor and are 1,1-difunctionalized.
View Article and Find Full Text PDFDalton Trans
August 2024
Department of Chemistry, Indian Institute of Technology, Kharagpur, 721 302, Kharagpur, India.
In this study, the reaction between 2-(3,5-dimethylpyrazolylmethyl)-5-(dimethylaminomethyl)pyrrole and thiophenol under heating conditions afforded the new ligand 2-(3,5-dimethylpyrazolylmethyl)-5-(phenylthiomethyl)pyrrole 2. The reaction of 2 with -chloroperbenzoic acid provided sulfoxide 3 and sulfone 4 group-containing ligands. The reaction of 2 with copper(I) halides provided the binuclear complexes [Cu(μ-X){μ-CHN-2-(CHMepz)-5-(CHSPh)-κ-S,N}] (X = Cl, Br and I, 5-7) in high yields.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!