Synlett 2011(9): 1281-1284  
DOI: 10.1055/s-0030-1260548
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Synthesis of Sulfonyl Amidines and β-Amino Sulfonyl Enamines under Transition-Metal-Free Conditions

Tingting Gao, Mingming Zhao, Xu Meng, Chuanbin Li, Baohua Chen*
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Gansu Lanzhou 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: chbh@lzu.edu.cn;
Further Information

Publication History

Received 15 March 2011
Publication Date:
29 April 2011 (online)

Abstract

Treatment of enamine and azide resulted in the formation of either sulfonyl amidine or β-amino sulfonyl enamine derivative in moderate to good yields. The reaction could proceed under catalyst-free conditions.

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10

Typical Procedure for the Preparation of 4-Methyl- N -[morpholino(phenyl)methylene]benzenesulfonamide (3): To a stirred solution of 4-(1-phenylvinyl)morpholine (0.1 mmol) and CH2Cl2 (0.1 mL), p-toluenesulfonyl azide (0.15 mmol) was added successively. The mixture was kept at r.t. under air and stirred for 20 min. The mixture was then extracted with EtOAc, dried over MgSO4 and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chroma-tography (PE-EtOAc, 1:1) to give the product 3 as a white solid. ¹H NMR (400 MHz, CDCl3): δ = 2.36 (s, 3 H), 3.11-3.13 (m, 2 H), 3.53-3.56 (m, 2 H), 3.76-3.78 (m, 2 H), 3.92-3.95 (m, 2 H), 7.12-7.16 (m, 4 H), 7.34-7.45 (m, 3 H), 7.49-7.51 (m, 2 H). ¹³C NMR (100 MHz, CDCl3): δ = 21.4, 45.0, 48.2, 66.3, 66.7, 126.5, 127.3, 128.4, 128.8, 130.0, 131.3, 140.6, 141.7, 165.8.