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Syntheses of biodynamic heterocycles: baker’s yeast-assisted cyclocondensations of organic nucleophiles and phenacyl chlorides

Abstract

Substituted phenacyl chlorides (1af) were cyclocondensed with nucleophiles thiourea (2a) and thiobenzamide (2b) in presence of baker’s yeast (Saccharomyces cerevisiae) as whole-cell enzyme source in acetonitrile at room temperature to obtain 4-(4-substituted phenyl)thiazol-2-amines (3af) and 4-(substituted phenyl)-2-phenylthiazoles (4af), respectively. Moreover, substituted phenacyl chlorides also reacted with nucleophiles 2-amino-1,3,4-thiadiazole (2c), o-phenylenediamine (2d), 1-amino-2-mercapto-5-phenyl triazole (2e), and pyridin-2-amine (2f) at room temperature in presence of baker’s yeast to give fused heterocycles 6-(4-substituted phenyl)-2-phenylimidazo[2,1-b][1,3,4]thiadiazoles (5af), 2-(4-substituted phenyl)quinoxalines (6af), 6-(4-substituted phenyl)-3-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines (7af), and 2-(4-substituted phenyl)H-imidazo[1,2-a]pyridines (8af), respectively. The experimental conditions for these cyclocondensations were optimized to obtain the biodynamic heterocycles in high yield. The unique features of this work are use of baker’s yeast as a cheap and readily available natural source of biocatalyst, noticeable rate acceleration, convenient route to products, cost effectiveness, and scalability.

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Acknowledgements

The authors are grateful to Professor D. B. Ingle for invaluable discussion and guidance. The authors are very grateful to CDRI, Lucknow for providing spectral facilities. L.D.K. is also grateful to U.G.C., New Delhi, India for financial assistance in the form of a UGC-NET Senior Research Fellowship.

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Correspondence to Ramrao A. Mane.

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Khillare, L.D., Pratap, U.R., Bhosle, M.R. et al. Syntheses of biodynamic heterocycles: baker’s yeast-assisted cyclocondensations of organic nucleophiles and phenacyl chlorides. Res Chem Intermed 43, 4327–4337 (2017). https://doi.org/10.1007/s11164-017-2880-0

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Keywords

  • Baker’s yeast
  • Cyclocondensations
  • Heterocycles