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An organocatalytic approach for the construction of 2,3-dihydrobenzofuran scaffold through a formal [4 + 1] annulation of 2-(2-nitrovinyl)phenols and α-bromoacetophenones in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) has been developed. This protocol could be easily performed in one mmol scale, giving a broad range of 2,3-dihydrobenzofuran derivatives in moderate to excellent yields and remarkable diastereoselectivity (>20 : 1 dr in general) with good functional group tolerance.
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http://dx.doi.org/10.1039/d4ob01406e | DOI Listing |
J Org Chem
April 2025
School of Pharmacy, Guizhou Provincial Engineering Technology Research Center for Chemical Drug R&D, Guizhou Medical University, 550014 Guiyang, P. R. China.
Herein, we reported a DBU-catalyzed cascade and sequential [1 + 2 + 3] annulation of malononitrile with α,β-unsaturated ketones to access polyfunctionalized cyclohexanes with high yield and excellent diastereoselectivity (>93% yield, >19:1 dr). Intriguingly, this appears to be the new strategy for using α,β-unsaturated ketones either as or synthon to react with dinucleophile synthon to construct six-membered carbocycles in one-pot manner. In addition, these synthesized compounds suppressed the growth of phytopathogenic fungi in vitro.
View Article and Find Full Text PDFOrg Biomol Chem
February 2025
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, P.R. China.
An organocatalytic approach for the construction of 2,3-dihydrobenzofuran scaffold through a formal [4 + 1] annulation of 2-(2-nitrovinyl)phenols and α-bromoacetophenones in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) has been developed.
View Article and Find Full Text PDFOrg Lett
August 2024
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, People's Republic of China.
A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed cascade annulation reaction between -quinamines and 3-formylchromones was developed, affording a series of benzopyrone-fused hydrobenzo[,]indoles in moderate to high yields with excellent diastereoselectivity.
View Article and Find Full Text PDFJ Org Chem
August 2024
School of Chemistry, University of Hyderabad, Hyderabad 500046, Telangana, India.
Dearomative annulation reaction of acyl-tethered benzothiazole bisnucleophiles with β'-acetoxy allenoates by switching the Lewis base is developed. The DBU-catalyzed reaction gives benzothiazole-fused 1,4-dihydropyridine carboxylates by (3 + 3) annulation chemoselectively. By contrast, the PR-catalyzed reaction gives benzothiazole-fused azepines by (4 + 3) annulation and cyclopentene carboxylates by (4 + 1) annulation; the ratio of the latter two products depends on the solvent.
View Article and Find Full Text PDFOrg Lett
December 2023
School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou 221116, China.
A copper(II)/DBU relay catalyzed annulation of α-carbonyl-γ-alkynyl sulfoxonium ylides as a new class of sulfoxonium ylide reagents with sulfonyl hydrazides is reported, enabling intramolecular oxygen migration to produce a series of -sulfonamido 2-isoindoles with good yields. The present annulation proceeded readily by combining the Cu(II)-catalyzed 6- oxo-cyclization with the DBU-catalyzed isochromene skeletal rearrangement, resulting in the formation of multiple new chemical bonds.
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