Copper-Catalyzed Three-Component One-Pot Synthesis of Substituted 2-Aryl-1,3-benzoselenazoles

Tao Su; Shishun Xie; Bifu Li; Jun Yan; Ling Huang; Xingshu Li

doi:10.1055/s-0034-1378934

Synlett, Table of Contents

Synlett 2015; 26(02): 215-220
DOI: 10.1055/s-0034-1378934

letter

Copper-Catalyzed Three-Component One-Pot Synthesis of Substituted 2-Aryl-1,3-benzoselenazoles

Tao Su

^aInstitute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. of China Fax: +86(20)39943051 Email: huangl72@mail.sysu.edu.cn Fax: +86(20)39943050 Email: lixsh@mail.sysu.edu.cn

,

Shishun Xie

^aInstitute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. of China Fax: +86(20)39943051 Email: huangl72@mail.sysu.edu.cn Fax: +86(20)39943050 Email: lixsh@mail.sysu.edu.cn

,

Bifu Li

^bCollege of Life Science and Technology, Southwest University for Nationalities, Chengdu, 610041, P. R. of China

,

Jun Yan

^aInstitute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. of China Fax: +86(20)39943051 Email: huangl72@mail.sysu.edu.cn Fax: +86(20)39943050 Email: lixsh@mail.sysu.edu.cn

,

Ling Huang*

^aInstitute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. of China Fax: +86(20)39943051 Email: huangl72@mail.sysu.edu.cn Fax: +86(20)39943050 Email: lixsh@mail.sysu.edu.cn

,

Xingshu Li*

^aInstitute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. of China Fax: +86(20)39943051 Email: huangl72@mail.sysu.edu.cn Fax: +86(20)39943050 Email: lixsh@mail.sysu.edu.cn

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Abstract

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Abstract

A simple copper-catalyzed, one-pot synthesis of 2-aryl-1,3-benzoselenazole derivatives was developed using inexpensive, readily available 2-iodoanilines, selenium powder, and aromatic aldehydes as the starting materials. The mild reaction conditions and simple procedure without ligands and other additives make this methodology an alternative for preparing these potential selenium-containing compounds very conveniently.

Key words

multicomponent reactions - heterocycle - 2-aryl-1,3-benzoselenazoles

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References

References and Notes
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32 Typical Procedure for the Synthesis of 2-Aryl-1,3-benzoselenazole 3aaTo a solution of 2-iodoaniline (0.5 mmol) and benzaldehyde (0.6 mmol) in dry DMSO (1.5 mL), selenium powder (1.5 mmol), catalyst (0.05 mmol), and KOH (1.0 mmol) were added, the reaction mixture was stirred in a sealed tube under argon atmosphere at 120 °C for 36 h. After the reaction was finished, the mixture was cooled to r.t., diluted with sat. aq NH₄Cl (15 mL), and extracted with EtOAc (3 × 10 mL). The organic layer was dried over Na₂SO₄, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography to afford the corresponding product 3aa. White solid; mp 116.2–117.1 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.12 (d, J = 8.0 Hz, 1 H), 8.06–7.98 (m, 2 H), 7.94 (d, J = 7.8 Hz, 1 H), 7.50–7.46 (m, 4 H), 7.31 (t, J = 7.5 Hz, 1 H). ¹³C NMR (101 MHz, CDCl₃): δ = 172.47, 155.85, 138.33, 136.20, 131.03, 129.06, 128.01, 126.39, 125.26, 124.86, 124.82. HRMS: m/z [M + H]⁺ calcd for C₁₃H₁₀NSe: 259.9973; found: 259.9948.

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