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Current Organic Chemistry

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ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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Short Communication

Ruthenium-catalyzed Aromatic meta-C-H Nitration of 1,2,4-thiadiazoles

Author(s): Kai Wang, Wenjing Xu, Pengfei Zhang* and Xian-Ting Cao*

Volume 26, Issue 19, 2022

Published on: 26 December, 2022

Page: [1807 - 1811] Pages: 5

DOI: 10.2174/1385272827666221216105255

Price: $65

Abstract

Aim and Objective: To develop a ruthenium-catalyzed method to prepare metanitration containing 1,2,4-thiadiazoles with potential biological activity. Moreover, the current protocol should exhibit a relatively broad substrate scope and functional group compatibility.

Materials and Methods: The best condition for the synthesis of nitration containing 1,2,4- thiadiazoles derivatives was carried out employing a mixture of 0.20 mmol of 1 (1a: 47.6 mg, 1b: 53.2 mg, 1c: 70.1 mg, 1d: 59.7 mg, 1e: 81.2 mg, 1f: 54.8 mg, 1g: 61.4 mg, 1h: 74.8 mg, 1i: 53.2 mg, 1j: 59.0 mg, 1k: 54.9 mg, 1l: 50.0 mg), Cu(NO3)2•3H2O (120.8 mg, 0.5 mmol), Ru3CO12 (9.6 mg, 7.5 mol %), TBAOAc (18.0 mg, 30 mol %), AgTFA (66.2 mg, 1.5 equiv), oxone (123.0 mg, 1.0 equiv), DCE (1.0 mL) placing in a Schlenk tube and stirred at 90 oC under air atmosphere for 36.0 h.

Results: A series of 1,2,4-thiadiazoles containing compounds with potential biological activity were prepared in yield ranging from moderate to good under mild conditions, exhibiting a relatively broad substrate scope and functional group compatibility.

Conclusion: We have developed a ruthenium-catalyzed 1,2,4-thiadiazoles-assisted regioselective meta-C-H nitration of arenes. This study provides a simple and efficient approach for synthesizing 1,2,4-thiadiazoles derivatives, yielding the nitration products in moderate to good yields. A mechanistic study indicated that a radical pathway might be involved in this transformation.

Keywords: Ruthenium-catalyzed, meta-C-H nitration, 1, 2, 4-thiadiazoles, potential biological activity, organic synthesis, radical pathway.

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