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BF3·OEt2 catalyzed base-free regiospecific ring opening of N-activated azetidines with (E)-1-arylidene-2-arylhydrazines

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Abstract

Making a C–N bond is always an interesting challenge for organic chemists. Azetidines are important nitrogen containing building blocks for synthesis of larger molecules. The first report of regiospecific addition of hydrazones to the benzylic position of aryl azetidines to afford high yields of important hydrazonyl amine derivatives is described herein. A new C–N bond forms in this reaction scheme. The reactions proceed at stellar rates in presence of only 5 mol% of BF3·OEt2 Lewis acid without the need of any base. The reaction requires easy-to-synthesize reagents and very mild condition. This report is a useful method to synthesize the building blocks of biologically active natural products containing one or more N–N bond(s).

Graphical Abstract

A base-free regiospecific ring opening of azetidines with various hydrazones is described to synthesize various hydrazonyl amines in a very short span of time. This report describes an aniline N-functionalization of hydrazines with a smooth C–N bond-forming reaction.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology, Kharagpur, 721 302, India

    Ranadeep Talukdar

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  1. Ranadeep Talukdar
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Correspondence to Ranadeep Talukdar.

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Dedicated to Professor Manas K. Ghorai on the occasion of his 51st birthday.

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Talukdar, R. BF3·OEt2 catalyzed base-free regiospecific ring opening of N-activated azetidines with (E)-1-arylidene-2-arylhydrazines. J IRAN CHEM SOC 16, 127–136 (2019). https://doi.org/10.1007/s13738-018-1489-6

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  • DOI: https://doi.org/10.1007/s13738-018-1489-6

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