Herein we report a new library of 2,3-pyrrolidinedione analogues that expands on our previous report on the antimicrobial studies of this heterocyclic scaffold. The novel 2,3-pyrrolidinediones reported herein have been evaluated against S. aureus and methicillin-resistant S. aureus (MRSA) biofilms, and this work constitutes our first report on the antibiofilm properties of this class of compounds. The antibiofilm activity of these 2,3-pyrrolidinediones has been assessed through minimum biofilm eradication concentration (MBEC) and minimum biofilm inhibition concentration (MBIC) assays. The compounds displayed antibiofilm properties and represent intriguing scaffolds for further optimization and development.

A teaching team composed of a faculty member (lecture) and a graduate teaching assistant (lab) endeavored to engage students enrolled in several sections of the same organic chemistry course through the use of social media. Students were encouraged to follow both instructors on Twitter and were asked to share aspects of the class using the social media site. Instructors regularly posted content and links relevant to the course and interacted with students, modeling professional social media interactions. Although the extent of student participation was limited, it was determined that this is a possible complementary outlet for class communication, sharing of information, and limited data gathering. In the lab courses, students were found to be more reticent to engage but did use the "follow" function to add the lab instructor to their Twitter networks. Lab and lecture courses were surveyed in order to determine factors affecting student engagement on social media. Results of the surveys and data collected in both courses are discussed with an emphasis on best practices.

By using an expanded set of 5-benzylidene-4-oxazolidinones it was possible to inhibit the formation of Staphylococcus aureus biofilms, disperse preformed biofilms and—in combination with common antibiotics—to significantly reduce the bacterial load in a robust collagen–matrix biofilm model. In addition to traditional resistance mechanisms, most chronic and recurring infections are further made tolerant to antibiotic action by the presence of biofilms and novel strategies to combat these bacterial communities are urgently needed. More information can be found in the communication by J. G. Pierce et al. on page 933 in Issue 7, 2020 (DOI: 10.1002/cbic.201900633).

The failure of frontline antibiotics in the clinic is one of the most serious threats to human health and requires a multitude of novel therapeutics and innovative treatment approaches to curtail the growing crisis. In addition to traditional resistance mechanisms resulting in the lack of efficacy of many antibiotics, most chronic and recurring infections are further made tolerant to antibiotic action by the presence of biofilms. Herein, we report an expanded set of 5-benzylidene-4-oxazolidinones that are able to inhibit the formation of Staphylococcus aureus biofilms, disperse preformed biofilms and in combination with common antibiotics are able to significantly reduce the bacterial load in a robust collagen-matrix model of biofilm infection.

Students in a large introductory organic chemistry class were given the freedom to choose an organic compound of interest and were challenged to develop an educational object (physical or digital) designed to be shared with the broader public via social media. Analysis of the project results shows that most students appreciated the open nature of the assignment, and engaged in self-regulated learning by reflecting and improving on their educational object design along each step of the project. Subjects varied widely depending on the students' personal interests, and many different educational objects were produced and shared using diverse social media outlets. As a result of this project, students reported positive outcomes including increased interest in organic chemistry and science in general as well as the acquisition of practical skills such as science communication and visual representation of science. These skills were perceived by students as being beneficial for future professional endeavors. This report describes the design and outcomes of the project, including the choice of subjects, representations, and social media channels.

Chloride, bromide and iodide are inhibitors of the copper-catalysed azide-alkyne cycloaddition, with iodide exhibiting the most detrimental effects on rates and yields. A study of this inhibition is presented, along with experimental protocols to accommodate the presence of halides in this widely used reaction.

Enaminones can be prepared via the Rh2(OAc)4-catalyzed coupling of α-diazocarbonyl compounds with thioamides. However, rhodium is the most expensive and least abundant among the dominant precious metals used for catalysis. Furthermore, a very limited substrate scope is known for the intermolecular rhodium catalyzed coupling reaction. Therefore, there is a need to find a more economical catalyst substitute with a broad substrate scope. In this paper, we describe the use of Ru(II) catalysts for the synthesis of enaminones. The reaction can be performed efficiently with the Grubbs first-generation catalyst or [(Ph)3P]3RuCl2 in a sealed tube. Both catalysts are much less expensive than Rh2(OAc)4. Secondary and tertiary thioamides, when reacted with α-diazodiesters, α-diazoketoesters, α-diazodiketones, and α-diazomonoketones give enaminones. Primary thioamides give thiazole derivatives when reacted with α-diazomonoketones. However, with other diazo compounds, primary thioamides also give enaminones. All enaminones are obtained in good yields and with good diastereoselectivity. Accordingly, the method described in this paper is an efficient and economical alternative to the Rh2(OAc)4-catalyzed coupling process.