Diazocarbonyl compounds have found numerous applications in many areas of chemistry. Among the most developed fields of diazo chemistry is the preparation of azoles from diazo compounds. This approach represents a useful alternative to more conventional methods of the synthesis of azoles. A comprehensive review on the preparation of various azoles (oxazoles, thiazoles, imidazoles, pyrazoles, triazoles, and tetrazoles) from diazocarbonyl and related compounds is presented for the first time along with discussion of advantages and disadvantages of «diazo» approaches to azoles.
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http://dx.doi.org/10.3390/molecules26092530 | DOI Listing |
Angew Chem Int Ed Engl
December 2024
Harvard University, Chemistry and Chemical Biology, 12 Oxford St., Mallinckrodt 303N, 02138, Cambridge, UNITED STATES OF AMERICA.
Sulfenyl fluorides are organic compounds of sulfur in formal oxidation state +2 with the formula R-S-F. Although the chloride, bromide, and iodide analogues have been extensively described in the literature, arenesulfenyl fluorides remain essentially unstudied. These structures have been implicated as putative intermediates in established processes to access polyfluorinated sulfur species; however, definitive and direct evidence of their existence has not been obtained, nor has a systematic understanding of their reactivity.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States.
A novel iridium-catalyzed [3 + 2] annulation of naphthylamines and α-diazocarbonyl compounds was developed for the rapid assembly of densely functionalized indoles. This new catalytic process represents the first example of a cascade intramolecular nucleophilic cyclization by the N-H insertion of amines. Various naphthylamines and α-diazocarbonyl compounds could be obtained in high yields with excellent functional group tolerance.
View Article and Find Full Text PDFOrg Biomol Chem
November 2024
College of Chemistry and Environmental Engineering, Shenzhen University, Shenzhen 518061, China.
Herein, the hydrogen halogenation reaction of diazo compounds with three new halogenating agents under photoinduced conditions is reported. This method realized hydrofluorination, hydrochlorination, and hydrobromination (56 cases in total, with the highest preparative yield of 94%) without requiring heating, transition metal catalysts or photocatalysts and exhibits a broad substrate scope. Notably, gram-scale synthesis using a continuous flow reactor was performed.
View Article and Find Full Text PDFACS Catal
October 2024
Department of Chemistry and Material Science, School of chemical Engineering, Aalto University, 02150 Espoo, Finland.
Org Biomol Chem
May 2024
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad-500037, India.
An efficient Rh(III)-catalysed C-H functionalization, tandem annulation of -stilbene acids using 2-diazo-1,3-diketones was devised. This protocol solely afforded 6,7-dihydrobenzofuran-4(5)-ones using alicyclic diazocarbonyls decarbonylation and α-pyrones with aliphatic diazo compounds. The chameleonic nature of -stilbene acid was observed with various diazo compounds by altering the additives.
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