[structure: see text]. Iodobenzene diacetate-mediated reactions of methylenecyclopropanes 1, vinylidenecyclopropanes 2, and a methylenecyclobutane 3a with phthalhydrazide give the corresponding [3+2] cycloaddition products in good yields under mild conditions. In these reactions, phthalhydrazide was transformed to a 1,3-dipole intermediate in the presence of iodobenzene diacetate. A plausible reaction mechanism has been proposed.
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http://dx.doi.org/10.1021/ol070178r | DOI Listing |
Molecules
December 2024
The Division of Chemical Biology and Medicinal Chemistry, College of Pharmacy, University of Texas at Austin, Austin, TX 78712, USA.
The hypervalent iodine-mediated formation of steroidal 5/5-spiroiminals and 5/5-spiroaminals from steroidal amines is presented. Under the influence of excess PhI(OAc) and iodine in acetonitrile at 0 °C, steroidal amines smoothly underwent cyclization to give a mixture of 5/5-spiroiminals and 5/5-spiroaminals. This reaction represents the first example of a C-H-activation-mediated formation of a spiroiminal.
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November 2024
Bioorganic & Biophysical Chemistry Laboratory, Linnaeus University Centre for Biomaterials Chemistry, Department of Chemistry & Biomedical Sciences, Linnaeus University, SE-39182 Kalmar, Sweden.
Unsymmetrical urea derivatives are essential structural motifs in a wide array of biologically significant compounds. Despite the well-established methods for synthesizing symmetrical ureas, efficient strategies for the synthesis of unsymmetrical urea derivatives remain limited. In this study, we present a novel approach for the synthesis of unsymmetrical urea derivatives through the coupling of amides and amines.
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November 2024
College of Chinese Medicine, the First Affiliated Hospital, and Key Laboratory of Xin'an Medicine of the Ministry of Education, Anhui University of Chinese Medicine, Hefei, 230038, P. R. China.
Metal-free radical cascade synthesis of substituted pyrazole derivatives was initiated by PhI(OAc) at 23 °C. This protocol features wide functional group tolerance, a simple purification process without column chromatography, and an oxygen migration. Compound 5 demonstrated significant anti-inflammatory activity, indicating potential for therapy.
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August 2024
Research Group of Bioorganic and Biocoordination Chemistry, University of Pannonia, H-8201 Veszprém, Hungary.
Nat Commun
March 2024
Bioorganic & Biophysical Chemistry Laboratory, Centre for Biomaterials Chemistry, Department of Chemistry & Biomedical Sciences, Linnaeus University, Kalmar, SE-39182, Sweden.
Hydrazides, N-N containing structural motifs, are important due to their presence in a wide variety of biologically significant compounds. While the homo N-N coupling of two NH moieties to form the hydrazide N-N bond is well developed, the cross-dehydrogenative hetero N-N coupling remains very unevolved. Here we present an efficient intermolecular N-N cross-coupling of a series of primary benzamides with broad range of Lewis basic primary and secondary amines using PhI(OAc) as both a terminal oxidant and a cross-coupling mediator, without the need for metal catalysts, high temperatures, and inert atmospheres, and with substantial potential for use in the late-stage functionalization of drugs.
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