Application of Saccharin as an Acidic Partner in the Ugi Reaction for the One-Pot Synthesis of 3-Iminosaccharins

Sorour Ramezanpour; Zahra Bigdeli; Nahid S. Alavijeh; Frank Rominger

doi:10.1055/s-0036-1558962

Synlett, Table of Contents

Synlett 2017; 28(10): 1214-1218
DOI: 10.1055/s-0036-1558962

letter

Application of Saccharin as an Acidic Partner in the Ugi Reaction for the One-Pot Synthesis of 3-Iminosaccharins

Sorour Ramezanpour*

^aPeptide Chemistry Research Center, K. N. Toosi University of Technology, P.O. Box 15875-4416, Tehran, Iran

,

Zahra Bigdeli

^aPeptide Chemistry Research Center, K. N. Toosi University of Technology, P.O. Box 15875-4416, Tehran, Iran

,

Nahid S. Alavijeh

^aPeptide Chemistry Research Center, K. N. Toosi University of Technology, P.O. Box 15875-4416, Tehran, Iran

,

Frank Rominger

^bOrganisch-Chemisches Institut der Universitaet Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany Email: Ramezanpour@kntu.ac.ir

› Author Affiliations

Abstract

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Dedicated to Prof. Dr. Saeed Balalaie on the occasion of his 50^th birthday

Abstract

The use of saccharin as a replacement for the carboxylic acid component in an Ugi multicomponent condensation leading to [(1,1-dioxido-1,2-benzisothiazol-3-yl)amino]acetamide (3-iminosaccharin) derivatives is described for the first time.

Key words

multicomponent reactions - condensation - Ugi reaction - saccharin - iminosaccharins

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References

References and Notes
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34 Saccharin Derivatives 10a–o; General Procedure A solution of aldehyde 6 (1 mmol), amine 7 (1 mmol), isocyanide 8 (1 mmol), and saccharin 9 (1 mmol) in EtOH (4 mL) was stirred for 24 h at r.t. while the progress of the reaction was monitored by TLC (hexane–EtOAc, 3:1). When the reaction was complete, the precipitate was collected by filtration and washed with EtOH. 2-[Benzyl(1,1-dioxido-1,2-benzisothiazol-3-yl)amino]-N-cyclohexyl-2-(4-methoxyphenyl)acetamide (10a) White powder; yield: 310 mg (60%); mp 247–250 °C (dec.). IR (KBr): 1308, 1549, 1673, 3310 cm⁻¹; ¹H NMR (300 MHz, CDCl₃): δ = 1.00–1.29 (m, 5 H, H_cHex), 1.50–1.70 (m, 5 H, H_cHex), 3.52–3.61 (m, 1 H, –CH, H_cHex), 3.63 (s, 3 H, –CH₃), 4.96 (d, J = 17.2 Hz, 1 H, CHN), 5.33 (d, J = 17.2 Hz, 1 H, CHN), 6.23 (s, 1 H, –CHN), 6.71 (d, J = 7.6 Hz, 2 H, H_Ar), 7.00 (d, J = 7.6 Hz, 2 H, H_Ar), 7.06–7.15 (m, 3 H, H_Ar), 7.20 (d, J = 8.6 Hz, 2 H, H_Ar), 7.50–7.62 (m, 2 H, H_Ar), 7.70–7.75 (m, 1 H, H_Ar), 8.03 (d, J = 7.5 Hz, 1 H, H_Ar), 8.24 (d, J = 6.1 Hz, 1 H, NH). ¹³C NMR (75 MHz, CDCl₃): δ = 24.5, 25.1, 32.0, 47.9, 55.1, 66.5, 113.5, 122.1, 125.7, 125.9, 126.2, 126.6, 126.8, 128.0, 131.6, 133.2, 133.4, 136.6, 143.8, 159.3, 161.7, 167.4. HRMS (ESI-POS): m/z [M + Na]⁺ calcd for C₂₉H₃₁N₃NaO₄S: 540.19406; found: 540.19386; [M + K]⁺ calcd for C₂₉H₃₁KN₃O₄S: 556.16847; found: 556.16820, [2M + Na]⁺calcd for C₅₈H₆₂N₆NaO₈S₂: 1057.39908; found: 1057.39884; [2M + K]⁺ calcd for C₅₈H₆₂KN₆O₈S₂: 1073.37378; found: 1073.37348.
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36 CCDC 1419875 contains the supplementary crystallographic data for 10a. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

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