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Substituted Indolizines via a Multicomponent 1,3-Dipolar Cycloaddition Strategy
S. Muthusaravanan, S. Perumal*, P. Yogeeswari, D. Sriram
Madurai Kamaraj University and Birla Institute of Technology and Science - Pilani, Hyderabad, India
21 December 2010 (online)
Reported is the synthesis of indolizines via a multicomponent domino reaction sequence starting from pyridines and isoquinolines, bromoacetonitrile or ethyl bromoacetate, and β-nitrostyrenes. The tolerance of the aryl component of the β-nitrostyrenes was investigated, showing little dependence on the aryl substitution pattern. Cyclizations employing isoquinolines and ethyl bromoacetate gave the denitrated products, whereas all other cases gave the nitro-substituted compounds. The activity of these compounds against M. tuberculosis H37RV was investigated with several compounds demonstrating higher activity than the standard first line TB drugs ethambutol and ciprofloxacin.