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The synthesis of benzo[]azepines using protonated aminating reagent (MsONHOTf) and alkynes through I-mediated [6 + 1] annulation reaction has been developed. This protocol features excellent functional group tolerance and mild reaction conditions and affords the benzo[]azepines in moderate to good yields under metal-free reaction conditions.
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http://dx.doi.org/10.1021/acs.orglett.3c00790 | DOI Listing |
J Org Chem
September 2024
X-ray Crystallography Center, Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, United States.
Highly strained [3.2.1] bicyclic twisted amide and corresponding amidium were synthesized for the first time through Ag(I)-mediated halide abstraction.
View Article and Find Full Text PDFJ Org Chem
August 2024
College of Chemistry and Molecular Science, Henan University, Kaifeng 475004, China.
An effective and straightforward Ag(I)-mediated annulation of 2-(2-enynyl)quinolines and -(2-alkynylbenzylidene)hydrazides was developed, forging various synthetically challenging 17-isoquinolino[2'',1'':1',6']pyridazino[4',5':3,4]pyrrolo[1,2-]quinolines, including different nitrogen-containing fused rings, in moderate to excellent yields. This one-pot cycloaddition strategy features exclusive regioselectivity, high atom economy, and broad substrate scope under mild conditions. The practicality and reliability of this cycloaddition reaction was demonstrated by a successful scale-up synthesis.
View Article and Find Full Text PDFJ Org Chem
January 2024
College of Chemistry and Molecular Science, Henan University, Kaifeng, Henan 475004, China.
An effective Ag(I)-mediated annulation of 2-(2-enynyl)pyridines and propargyl amines was developed, unexpectedly affording a broad range of functionalized 1-(2-pyrrol-3-yl)indolizines in moderate to excellent yields. The developed method is characterized by operational simplicity, ready availability of starting materials, high regioselectivity, and broad substrate scope under mild reaction conditions. The Ag(I)-promoted cyclization of 2-(2-enynyl)pyridines and propargyl amines possibly results in the formation of the spiroindolizine, the ring-opening rearrangement of which may give the 1-(2-pyrrol-3-yl)indolizine.
View Article and Find Full Text PDFJ Org Chem
December 2021
Department of Chemistry, Indian Institute of Technology Guwahati, Guwaha, Assam 781039, India.
A Cu(I)-mediated cascade cyclization/annulation of unprotected -alkynylanilines with maleimides in one pot is developed. The protocol offers sequential formation of one C-N and two C-C bonds to deliver fused benzo[]carbazoles having free NH skeletons. The annulated products display fluorescence emission in the range of 485-502 nm with a large Stokes shift and fluorescence lifetime of ∼17 ns.
View Article and Find Full Text PDFOrg Biomol Chem
October 2021
School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou, 510006, P. R. China.
An efficient and practical approach for the synthesis of medicinally important acridones was developed from anthranils and commercially available arylboronic acids by a tandem copper(I)-catalyzed electrophilic amination/Ag(I)-mediated oxidative annulation strategy. This new and straightforward protocol displayed a broad substrate scope (25 examples) and high functional group tolerance. What's more, a possible mechanistic proposal was also presented.
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