121044-64-2Relevant academic research and scientific papers
7-Oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-Dioxides: Mechanochemical Synthesis by Tandem Michael Addition–1,3-Dipolar Cycloaddition of Aldoximes and Evaluation of Antibacterial Activities
Bhutia, Zigmee T.,Das, Avijit,Biswas, Malabika,Chatterjee, Amrita,Banerjee, Mainak
, p. 506 - 514 (2018/02/09)
A solvent-free, green, and efficient mechanochemical method for the synthesis of a series of bridged bicyclo aza-sulfone derivatives, namely 7-oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-dioxides through tandem Michael addition–1,3-dipolar cycloaddition of aldoximes was developed. Mechanochemical grinding/milling facilitates quick formation of aldoximes from corresponding aldehydes and hydroxylamine, which upon reaction with divinyl sulfone in a mixer mill affords 7-oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-dioxide derivatives in good overall yields. The newly synthesized bicyclo aza-sulfone derivatives 4 were screened for antibacterial activities. Mostly bicyclo aza-sulfones derived from electron-rich aromatic aldehydes inhibit the growth of Mycobacterium smegmatis (mc2155) and those from aliphatic aldehydes the growth of Escherichia coli (DH5α) in moderate to good effect. However, butyraldehyde-derived compound 4r was very effective against both M. smegmatis and E. coli. The key advantages of this mechanochemical method are catalyst- and solvent-free conditions, shorter reaction time, and formation of a new series of 7-oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-dioxide derivatives, which are good antibacterial agents against M. smegmatis and E. coli.
X=Y-ZH systems as potential 1,3-dipoles. Part 34. Generation of nitrones from oximes. Tandem Michael addition-1,3-dipolar cycloaddition reactions. Class 2 processes utilising bifunctional Michael acceptor-dipolarophile components
Grigg, Ronald,Dorrity, Michael J.,Heaney, Frances,Malone, John F.,Rajviroongit, Shuleewan,Sridharan, Visuvanathar,Surendrakumar, Sivagnanasundram
, p. 8297 - 8322 (2007/10/02)
Aldoximes and ketoximes react with a range of bifunctional Michael acceptor-dipolarophile substrates comprising functionalised 1,3-, 1,4- and 1,5-dienes via a tandem process involving an N-alkenyl nitrone intermediate. The 1,3-dienes react regio- and stereo-specifically to give 1-aza-7-oxabicyclo[2.2.1]heptanes whilst sterically unencumbered aryl aldoximes and 1,4-dienes give 1-aza-2-oxabicyclo[3.2.1]octane derivatives. Ketoximes and 1.4-dienesgive mixtures of 1-aza-2-oxa- and 1-aza-8-oxa-bicyclo[3.2.1]octanes. 1,5-Dienes and ketoximes react regio-and stereo-specifically to give 1-aza-8-oxabicyclo[3.2.1]octane derivatives whilst benzaldoxime gives a 1:1 mixture of epimeric 1-aza-8-oxabicyclo[3.2.1]octanes together with traces of two epimeric 1-aza-2-oxabicyclo[3.2.1]octanes. The regio- and stereo-chemical outcome of the tandem process is controlled by the length and nature of the linking chain in the bifunctional substrate and the steric interactions between substituents on the oxime and dipolarophile in the transition state. A crystal structure of one of the 1-aza-7-oxabicyclo[2.2.1]heptanes is reported.
REGIO- AND STEREO-SPECIFIC CLASS 2 TANDEM MICHAEL ADDITION-CYCLOADDITION REACTIONS OF OXIMES
Grigg, Ronald,Malone, John F.,Dorrity, Michael R. J.,Heaney, Frances,Rajviroongit, Shuleewan,et al.
, p. 4323 - 4324 (2007/10/02)
Oximes react regio- and stereo-specifically with 1,3- , 1,4- and 1,5-dienes bearing electronegative substituents via a tandem Michael addition-1,3-dipolar cycloaddition process to give bridged ring cycloadducts in good yield.
