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La(OTf)3-catalyzed one-pot synthesis of meso-substituted porphyrinic thiazolidinones

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Abstract

An improved synthetic procedure is developed for the regioselective nitration of a phenyl group of meso-tetraphenylporphyrin by using NaNO2 in a mixture of trichloroacetic acid and AcOH. The meso-(4-nitrophenyl)porphyrins are successfully reduced to corresponding meso-(4-aminophenyl)porphyrins by SnCl2 under acidic conditions. In addition, an efficient one-pot methodology for synthesizing a series of novel meso-substituted porphyrinic thiazolidinone conjugates is developed by reacting meso-(4-aminophenyl)porphyrins with various aromatic aldehydes and mercaptoacetic acid in refluxing toluene using La(OTf)3 as a catalyst. The products obtained are characterized on the basis of their spectral data. Preliminary photophysical properties of the newly synthesized compounds are reported.

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Acknowledgments

We thank the University of Delhi, India, for providing financial support. Satyasheel is grateful to Council of Scientific and Industrial Research, New Delhi, India, for the Junior Research Fellowship.

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Authors and Affiliations

  1. Department of Chemistry, University of Delhi, Delhi, 110 007, India

    Ranjan K. Bhatt, Satyasheel Sharma & Mahendra Nath

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  1. Ranjan K. Bhatt
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  2. Satyasheel Sharma
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  3. Mahendra Nath
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Correspondence to Mahendra Nath.

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Bhatt, R.K., Sharma, S. & Nath, M. La(OTf)3-catalyzed one-pot synthesis of meso-substituted porphyrinic thiazolidinones. Monatsh Chem 143, 309–316 (2012). https://doi.org/10.1007/s00706-011-0625-0

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  • DOI: https://doi.org/10.1007/s00706-011-0625-0

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