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Synlett 2014; 25(07): 959-960
DOI: 10.1055/s-0033-1340836
letter
© Georg Thieme Verlag Stuttgart · New York

Sulfonoketenimides as Key Intermediates for the Synthesis of N-Tosyl-acetoyloxy Alkanimines

Issa Yavari*
Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran   Fax: +98(21)82883455   Email: yavarisa@modares.ac.ir
,
Majid Ghazanfarpour-Darjani
Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran   Fax: +98(21)82883455   Email: yavarisa@modares.ac.ir
,
Mohammad J. Bayat
Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran   Fax: +98(21)82883455   Email: yavarisa@modares.ac.ir
,
Alaleh Malekafzali
Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran   Fax: +98(21)82883455   Email: yavarisa@modares.ac.ir
› Author Affiliations
Further Information

Publication History

Received: 25 January 2013

Accepted: 28 January 2014

Publication Date:
14 March 2014 (online)

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Abstract

A copper-catalyzed multicomponent reaction between terminal alkynes, sulfonyl azides, and oximes for the synthesis of N-tosylacetoyloxy alkanimines is reported. This one-pot procedure is carried out in the presence of copper(I) iodide in acetonitrile at room temperature.

Key words

alkanimines - terminal alkyne - sulfonyl azide - oxime - copper iodide

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
  • Supporting Information
 

  • References and Notes

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  • 15 Typical Procedure for the Preparation of Products 4a–i To a stirred solution of alkyne (1, 1.0 mmol), sulfonylazide (2, 1.0 mmol), and CuI (19 mg, 0.10 mmol) in MeCN (2 mL) was added Et3N (1.5 mL) under argon at r.t. After 10 min, oxime (3, 1.2 mmol) was added, and the mixture was stirred for 4 h. The solvent was removed, the residue treated with of sat. aq NH4Cl (3 mL) and extracted with EtOAc (3 × 5 mL). Organic layers were combined, dried over anhydrous Na2SO4, and concentrated under vacuum. The residue was purified by chromatography (silica gel, hexane–EtOAc = 2:1) to give 4. 4-Methyl-N-[(-phenylmethyleneaminooxy)phenyl-ethylidene]benzenesulfonamide (4a) Colorless solid, mp 156–158 °C; yield 0.34 g (87%). IR (KBr): νmax = 3020, 2972, 1569, 1528, 1335, 1128 cm–1. 1H NMR (500.1 MHz, CDCl3): δ = 2.44 (3 H, s, CH3), 3.60 (2 H, s, CH2), 7.14 (2 H, d, 3 J = 8.9 Hz, 2 CH), 7.31–7.48 (8 H, m, 8 CH), 7.82 (2 H, 3 J = 8.5 Hz, 2 CH), 7.88 (2 H, d, 3 J = 8.2 Hz, 2 CH), 7.97 (1 H, s, CH). 13C NMR (125.7 MHz, CDCl3): δ = 21.7 (CH3), 43.8 (CH2), 126.1 (2 CH), 128.1 (CH), 128.5 (2 CH), 128.8 (2 CH), 129.0 (2 CH), 129.3 (CH), 129.4 (2 CH), 129.6 (2 CH), 133.7 (C), 137.5 (C), 141.0 (C), 143.2 (CH), 154.5 (CH), 165.9 (C). MS (EI): m/z (%) = 392 (5) [M+], 271 (13), 251 (100), 140 (10), 104 (14), 77 (60), 76 (42), 64 (44). Anal. Calcd (%) for C22H20N2O3S (392.47): C, 67.33; H, 5.14; N, 7.14. Found: C, 67.75; H, 5.19; N, 7.21.
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