In:
European Journal of Organic Chemistry, Wiley, Vol. 2018, No. 4 ( 2018-01-31), p. 506-514
Abstract:
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 (mc 2 155) 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 .
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2018.4
DOI:
10.1002/ejoc.201701511
Language:
English
Publisher:
Wiley
Publication Date:
2018
detail.hit.zdb_id:
1475010-7
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