Sulfur-Directed α-C(sp3)-H Amidation of Pyrrolidines with Dioxazolones under Rhodium Catalysis.

Site-selective functionalization of saturated N-heterocycles such as pyrrolidines is a central topic in organic synthesis and drug discovery. We herein report the sulfur-assisted rhodium(III)-catalyzed sp3 C-H amidation of pyrrolidines with dioxazolones as amidating agents. The amenability of the thioamide directing group is elucidated by a series of control experiments.

Rhodium(III)-Catalyzed Conjugate Addition of ß-CF3-Enones with Quinoline N-Oxides.

The site-selective incorporation of a trifluoromethyl group into biologically active molecules and pharmaceuticals has emerged as a central topic in medicinal chemistry and drug discovery. Herein, we demonstrate the rhodium(III)-catalyzed conjugate addition of ß-trifluoromethylated enones with quinoline N-oxides, which result in the generation of ß-trifluoromethyl-ß'-quinolinated ketones. The reaction proceeds under mild conditions with complete functional group tolerance. The synthetic applicability was showcased by successful gram-scale experiments and valuable synthetic transformations of coupling products.

Extraction sockets: erratic healing impeding factors.

AIM: The aim of this exploratory study was to analyse prevalence of extraction sockets showing erratic healing and evaluate factors potentially impeding healing. METHODS: Erratic healing was defined as extraction sites showing clinical observations of fibrous scar tissue occupying the extraction site rather than bone following 12 or more weeks of healing. Computerized tomography was used to evaluate characteristics and calculate Hounsfield unit scores for sites showing erratic healing. RESULTS: A total of 1226 dental records from Seoul National University Dental Hospital archives including patients subject to extractions prior to implant placement were evaluated. Seventy subjects (5.71%) and 97 sites (4.24%) exhibited erratic extraction socket healing. Maxillary incisor/canine sites showed the lowest (0.47%), whereas mandibular molar sites the highest (5.41%) occurrence. In the multivariable analysis, erratic healing was more likely to occur in subjects <60 years old (OR = 2.23, 95%CI = 1.26-3.94), subjects with hypertension (OR = 2.37, 95%CI = 1.24-4.55), in molar sites (OR = 4.91, 95%CI = 1.41-17.07), and following single tooth extractions (OR = 2.98, 95%CI = 1.36-6.53). Computerized tomography showed the highest incidence of bone loss for the buccal wall (49.3%). CONCLUSION: Erratic extraction socket healing appears a not uncommon sequel and local factors seem to be major contributors to its occurrence.