The Catalytic Synthesis of Carboniolamide: The Role of sp3 Hybridized Oxygen

Yi Zhang; Yuchi Dai; Guigen Li; Xu Cheng

doi:10.1055/s-0034-1379101

Synlett, Table of Contents

Synlett 2014; 25(18): 2644-2648
DOI: 10.1055/s-0034-1379101

letter

The Catalytic Synthesis of Carboniolamide: The Role of sp ³ Hybridized Oxygen

Yi Zhang

^aInstitute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P. R. of China

,

Yuchi Dai

^aInstitute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P. R. of China

,

Guigen Li

^aInstitute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P. R. of China

^bDepartment of Chemistry and Biochemistry, Texas Tech University, Memorial Circle & Boston, Lubbock, TX 79409-1061, USA Fax: +86(25)84687372 Email: chengxu@nju.edu.cn

,

Xu Cheng*

^aInstitute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P. R. of China

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Abstract

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Abstract

A catalytic synthesis of carboniolamide has been reported. The strategy was straightforward with aldehyde and amide as starting materials. The products can be isolated as precipitates from the reaction mixture. The factor that stabilizes the labile functionality of hemiaminal was elucidated as a sp ³ hybridized oxygen.

Key words

catalysis - amide - aldehyde - phosphate - nucleophilic addition

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References

References and Notes
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28 General Procedure for the Synthesis of the Carboniolamide: To a reaction vial charged with amide (1.0 mmol), glyoxylate (1.0 mmol), and diphenyl hydrogen phosphate (25.0 mg, 0.1 mmol) was added Et₂O (4 mL). Then the sealed reaction mixture was stirred at r.t. for the specified time. The obtained slurry was then filtered, and the precipitate was washed with a minimum amount of cold Et₂O to give the compound as a white powder. 1g: mp 106.2–108.1 °C. ¹H NMR (400 MHz, DMSO-d ₆): δ = 9.46 (d, J = 7.8 Hz, 1 H), 7.92 (d, J = 8.5 Hz, 2 H), 7.56 (d, J = 8.5 Hz, 2 H), 6.63 (d, J = 6.1 Hz, 1 H), 5.64 (t, J = 6.9 Hz, 1 H), 4.15 (q, J = 7.1 Hz, 2 H), 1.21 (t, J = 7.1 Hz, 3 H). ¹³C NMR (101 MHz, DMSO-d ₆): δ = 170.26, 165.43, 137.01, 132.72, 129.93, 128.92, 72.44, 61.25, 14.49. IR (thin film): 1015, 1033, 1102, 1155, 1239, 1312, 1345, 1487, 1536, 1598, 1649, 1655, 1746, 3304, 3402 cm^–1. MS (ESI): m/z [M + Na⁺] calcd for C₁₁H₁₂ClNO₄Na: 280; found: 280. HRMS (ESI): m/z [M + Na⁺] calcd for C₁₁H₁₂ClNO₄Na: 280.0353; found: 280.0356. 1n: mp 125.3–127.1 °C. ¹H NMR (400 MHz, DMSO-d ₆): δ = 8.43 (d, J = 8.6 Hz, 1 H), 7.90 (d, J = 7.5 Hz, 2 H), 7.74 (t, J = 8.1 Hz, 2 H), 7.32–7.45 (m, 4 H), 6.50 (s, 1 H), 5.29 (d, J = 8.6 Hz, 1 H), 4.20–4.36 (m, 3 H), 4.13 (q, J = 7.1 Hz, 2 H), 1.21 (t, J = 7.1 Hz, 3 H). ¹³C NMR (101 MHz, DMSO-d₆ ): δ = 170.04, 155.92, 144.24, 144.14, 141.18, 128.14, 127.54, 125.83, 125.76, 120.59, 73.73, 66.34, 61.25, 46.94, 14.47. IR (thin film): 740, 758, 1042, 1093, 1224, 1267, 1331, 1449, 1530, 1703, 1721, 1753, 3328 cm^–1. MS (ESI): m/z [M – H⁺] calcd for C₁₉H₁₉NO₅: 340; found: 340. HRMS (ESI): m/z [M + Na⁺] calcd for C₁₉H₁₉NO₅Na: 364.1161; found: 364.1163.
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Supplementary Material

Supporting Information

The Catalytic Synthesis of Carboniolamide: The Role of sp 3 Hybridized Oxygen

The Catalytic Synthesis of Carboniolamide: The Role of sp ³ Hybridized Oxygen