An Efficient One-Pot Synthesis of Benzo[1,4]Thiazines, Benzo[1,3]Thiazoles and Benzo[1,5]Thiazepines

Author(s): Ahmed F. M. El-Mahdy, Omima S. Mohamed, Hassan A.H. El-Sherif, Zeniab A. Hozien

Journal Name: Current Organic Synthesis

Volume 14 , Issue 4 , 2017


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Abstract:

Background: One-pot reactions have gained considerable and wide range of interests in the field of chemistry due to their simplicity and economy. Comparing to the step-by-step reactions that involve the formation of individual bonds for a given target product, the greatest attribute of one-pot reactions, is the formation of several bonds in one-pot operation without intermediate isolation, reaction condition changing and further reagents adding.

Objective: We developed an one-pot, rapid, simple and eco-friendly synthetic strategy for benzothiazines, benzothiazoles and benzothiazpines through the interaction of o-aminothiophenol with ketones, nitriles and chalcones, respectively.

Method: A mixture of o-aminothiophenol ketones, nitriles and chalcones was refluxed or stirred at room temperature in glacial acetic acid containing a catalytic amount of concentrated H2SO4 for 3h. Then, the resulting precipitate was collected by filtration, washed with water and crystallized from the appropriate solvent.

Results: The interaction of o-aminothiophenol with aromatic and aliphatic ketones containing active -hydrogens afforded the corresponding 2H-benzo[1,4]thiazines and 4H-benzo[1,4]thiazines, respectively. Similarly, the cyclic ketones afforded the corresponding tricyclic compounds. Treatment of o-aminothiophenol with nitriles under the same reaction condition gave benzo[1,3]thiazoles. Further, cyclocondensation with chalcones under the same reaction condition at room temperature yielded the corresponding benzo[1,5]thiazepines. The reaction mechanism was investigated and the structures of all new compounds were elucidated using spectral analysis.

Conclusion: An efficient, simple and environmentally friendly synthesis of benzothiazines, benzothiazoles and benzothiazepines in one-pot synthesis has been developed. With this catalytic reaction, a very cheap sulfuric acid was used as a catalyst.

Keywords: o-aminothiophenols, benzothiazines, benzothiazoles, benzothiazepines, one-pot reaction, economic preparation.

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Article Details

VOLUME: 14
ISSUE: 4
Year: 2017
Page: [604 - 611]
Pages: 8
DOI: 10.2174/1570179413666160624082057
Price: $65

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