64124-54-5Relevant academic research and scientific papers
Tandem 1,3-dipolar cycloaddition of mesoionic 2,4-diphenyl-1,3- oxathiolium-5-olate with cycloocta-1,5-diene. A new synthesis of the tetracyclo[6.2.0.04,10.05,9]decane ring system
Sponholtz Iii, William R.,Trujillo, Hernando A.,Gribble, Gordon W.
, p. 1687 - 1690 (2000)
The mesoionic heterocycle 2,4-diphenyl-1,3-oxathiolium-5-olate (5) undergoes a tandem 1,3-dipolar cycloaddition reaction with cycloocta-1,5- diene (6) to give cycloadduct sulfide 7 in modest yield. Oxidation to sulfone 8 and photochemical extrusion of SO2 affords 9,10- diphenyltetracyclo[6.2.0.04,10.05,9]decane (9) in high yield. (C) 2000 Elsevier Science Ltd.
Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) Hubs
Barrow, Andrew S.,Cheng, Yunfei,Gialelis, Timothy L.,Giel, Marie-Claire,Kitamura, Seiya,Li, Gencheng,Moses, John E.,Ottonello, Alessandra,Sharpless, K. Barry,Smedley, Christopher J.,Wolan, Dennis W.
supporting information, p. 12460 - 12469 (2020/06/10)
Diversity Oriented Clicking (DOC) is a unified click-approach for the modular synthesis of lead-like structures through application of the wide family of click transformations. DOC evolved from the concept of achieving “diversity with ease”, by combining classic C?C π-bond click chemistry with recent developments in connective SuFEx-technologies. We showcase 2-Substituted-Alkynyl-1-Sulfonyl Fluorides (SASFs) as a new class of connective hub in concert with a diverse selection of click-cycloaddition processes. Through the selective DOC of SASFs with a range of dipoles and cyclic dienes, we report a diverse click-library of 173 unique functional molecules in minimal synthetic steps. The SuFExable library comprises 10 discrete heterocyclic core structures derived from 1,3- and 1,5-dipoles; while reaction with cyclic dienes yields several three-dimensional bicyclic Diels–Alder adducts. Growing the library to 278 discrete compounds through late-stage modification was made possible through SuFEx click derivatization of the pendant sulfonyl fluoride group in 96 well-plates—demonstrating the versatility of the DOC approach for the rapid synthesis of diverse functional structures. Screening for function against MRSA (USA300) revealed several lead hits with improved activity over methicillin.
