98%
921
2 minutes
20
Herein we report a simple BF-catalyzed cycloaddition of dihydropyridines with bicyclobutanes for the expedient synthesis of novel three-dimensional azacycle-fused bicyclo[2.1.1]hexane scaffolds. The reaction utilizes easily accessible starting materials and proceeds under mild, metal-free conditions with high atom efficiency.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1039/d4cc06133k | DOI Listing |
J Org Chem
February 2025
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
Here, we revealed a convenient synthetic protocol for unique pyrido[2,3-]pyridazine and pyrido[3,2-][1,2]oxazine scaffolds with excellent regioselectvity and diastereoselectivity. The functionalized pyrido[2,3-] pyridazines were successfully synthesized via a CsCO-promoted [4 + 2] cycloaddition reaction of α-halogenated tosylhydrazones or acylhydrazones and 5,6-unsubstituted 1,4-dihydropyridines under mild conditions. Additionally, the similar base-promoted [4 + 2] cycloaddition reaction of α-chlorogenated oximes and 5,6-unsubstituted 1,4-dihydropyridines afforded functionalized pyrido[3,2-][1,2]oxazines in satisfactory yields.
View Article and Find Full Text PDFChem Commun (Camb)
January 2025
Organisch-Chemisches Institut, Universität Münster, Corrensstraße 40, 48149 Münster, Germany.
Herein we report a simple BF-catalyzed cycloaddition of dihydropyridines with bicyclobutanes for the expedient synthesis of novel three-dimensional azacycle-fused bicyclo[2.1.1]hexane scaffolds.
View Article and Find Full Text PDFChem Commun (Camb)
November 2024
Department of Chemistry, University of Victoria, 3800 Finnerty Rd., Victoria, BC, V8P 5C2, Canada.
Diastereoselective (3+3) cycloaddition between bicyclobutanes and pyridinium ylides forms azabicyclo[3.1.1]heptanes pyridine dearomatization.
View Article and Find Full Text PDFChem Sci
September 2024
Department of Chemistry, Graduate School of Science, The University of Tokyo Hongo Bunkyo-ku Tokyo 113-0033 Japan
Beilstein J Org Chem
June 2024
College of Chemistry & Chemical Engineering, Yangzhou University, Jiangsu, Yangzhou 225002, China.
An efficient protocol for the synthesis of polyfunctionalized tetrahydrocyclopenta[4,5]pyrrolo[2,3-]pyridine-3,4b,5,6,7(1)-pentacarboxylates was developed by a three-component reaction. In the absence of any catalyst, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 5,6-unsubstituted 1,4-dihydropyridines in refluxing acetonitrile afforded polyfunctionalized tetrahydrocyclopenta[4,5]pyrrolo[2,3-]pyridine-3,4b,5,6,7(1)-pentacarboxylates in high yields and with high diastereoselectivity. The reaction was finished by in situ generation of activated 5-(alkylimino)cyclopenta-1,3-dienes from addition of alkyl isocyanide to two molecules of but-2-ynedioates and sequential formal [3 + 2] cycloaddition reaction with 5,6-unsubstituted 1,4-dihydropyridine.
View Article and Find Full Text PDF