Abstract
A new and novel class of bis(heterocycles) viz., bis pyrroles, pyrrolyl pyrazoles and pyrrolyl isoxazoles are prepared from 1-aroyl-2-styrylsulfonylethenes by 1,3-dipolar cycloaddition of tosylmethyl isocyanide, diazomethane, nitrile imines and nitrile oxides. The lead compounds are screened for antimicrobial activity.
Highlights
In the last few decades the chemistry of five-membered heterocycles pyrroles, pyrazolines and isoxazolines has received considerable attention owing to their synthetic and effective biological importance
Literature evidenced the synthesis of 3,4-disubstituted pyrroles by cyclocondensation of Michael acceptors with tosylmethyl isocyanide (TosMIC) [9]
The synthetic scheme is based on the reactivity of 1-aroyl-2-styrylsulfonylethene (1) towards 1,3-dipolar reagents viz., TosMIC, diazomethane, nitrile imines, nitrile oxides
Summary
In the last few decades the chemistry of five-membered heterocycles pyrroles, pyrazolines and isoxazolines has received considerable attention owing to their synthetic and effective biological importance. Celecoxib, a pyrazole derivative and Valdecoxib an isoxazole derivative are extensively used as anti-inflammatory drugs [3]. It is thought that a worthwhile programme would be to prepare molecules having both pyrrole and pyrazole/isoxazole units. Diazomethane, nitrile imines and nitrile oxides have been used extensively as reactive intermediates. The nitrile imines and nitrile oxides can be generated by dehydrogenation of araldehyde phenylhydrazones and araldoximes with lead tetraacetate [16], mercuric acetate [17], 1-chlorobenzotriazole [18], chloramine-T [19,20,21,22] etc. The present communication deals with the synthesis of sulfone linked bis heterocycles having a pyrrole in combination with a pyrazole or an isoxazole unit
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