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Synlett 2014; 25(09): 1257-1262
DOI: 10.1055/s-0033-1341108
letter
© Georg Thieme Verlag Stuttgart · New York

Convenient Synthesis of 5-Arylidene-2-imino-4-thiazolidinone Derivatives Using Microwave Irradiation

Manal Sarkis
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS UMR 8601, Université Paris Descartes, PRES Sorbonne Paris Cité, 45 rue des Saints-Pères, 75006 Paris, France   Fax: +33(1)42864082   eMail: emmanuelle.braud@parisdescartes.fr
,
Diem-Ngan Tran
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS UMR 8601, Université Paris Descartes, PRES Sorbonne Paris Cité, 45 rue des Saints-Pères, 75006 Paris, France   Fax: +33(1)42864082   eMail: emmanuelle.braud@parisdescartes.fr
,
Maria Chiara Dasso Lang
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS UMR 8601, Université Paris Descartes, PRES Sorbonne Paris Cité, 45 rue des Saints-Pères, 75006 Paris, France   Fax: +33(1)42864082   eMail: emmanuelle.braud@parisdescartes.fr
,
Christiane Garbay
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS UMR 8601, Université Paris Descartes, PRES Sorbonne Paris Cité, 45 rue des Saints-Pères, 75006 Paris, France   Fax: +33(1)42864082   eMail: emmanuelle.braud@parisdescartes.fr
,
Emmanuelle Braud*
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS UMR 8601, Université Paris Descartes, PRES Sorbonne Paris Cité, 45 rue des Saints-Pères, 75006 Paris, France   Fax: +33(1)42864082   eMail: emmanuelle.braud@parisdescartes.fr
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Publikationsverlauf

Received: 07. Februar 2014

Accepted after revision: 13. März 2014

Publikationsdatum:
03. April 2014 (online)

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Abstract

A concise approach for the preparation of 5-arylidene-2-imino-4-thiazolidinone derivatives is described. Structurally diverse amines, isothiocyanates, aldehydes, and chloroacetyl chloride were combined under microwave irradiation to afford new 5-arylidene-2-imino-4-thiazolidinone derivatives. The one-pot synthesis involves the in situ formation of a thiourea followed by reaction with chloroacetyl chloride and an aldehyde to generate the target compounds.

Key words

5-arylidene-2-imino-4-thiazolidinone - thiourea - microwave irradiation - multicomponent reaction - Knoevenagel condensation

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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  • 29 Selected Analytical Data Compound 1: pale yellow solid (106 mg, 45%); mp 143–145 °C. 1H NMR (250 MHz, CDCl3): δ = 3.81 (s, 3 H, CH3), 3.84 (s, 3 H, CH3), 3.88 (s, 3 H, CH3), 4.60 (s, 2 H, CH2), 5.04 (s, 2 H, CH2), 6.84 (d, 2 H, J = 6.2 Hz, ArH), 6.91 (d, 2 H, J = 6.5 Hz, ArH), 7.00 (d, 2 H, J = 6.5 Hz, ArH), 7.26 (d, 2 H, J = 6.2 Hz, ArH), 7.47 (d, 2 H, J = 6.5 Hz, ArH), 7.51 (d, 2 H, J = 6.5 Hz, ArH), 7.73 (s, 1 H, C=CH). 13C NMR (63 MHz, CDCl3): δ = 45.5, 55.2, 55.3, 55.4, 55.8, 113.7 (2 C), 113.8 (2 C), 114.5 (2 C), 118.8, 126.6, 128.6 (2 C), 128.8, 130.0, 130.5 (2 C), 131.3, 131.8 (2 C), 149.0, 158.6, 159.2, 160.7, 166.9. IR: ν = 2951, 2829, 1697, 1644, 1615, 1599, 1509, 1468, 1443, 1426, 1380, 1338, 1297, 1249, 1173, 1163, 1117, 1106, 1032 cm–1. ESI-HRMS: m/z calcd for C27H27N2O4S [M + H]+: 475.1692; found: 475.1707. Compound 2: yellow solid (134 mg, 55%); mp 169–170 °C. 1H NMR (250 MHz, CDCl3): δ = 2.54 (s, 3 H, CH3), 3.81 (s, 3 H, CH3), 3.84 (s, 3 H, CH3), 4.61 (s, 2 H, CH2), 5.05 (s, 2 H, CH2), 6.84 (d, 2 H, J = 6.5 Hz, ArH), 6.91 (d, 2 H, J = 6.5 Hz, ArH), 7.25–7.33 (m, 4 H, ArH), 7.47 (d, 2 H, J = 8.0 Hz, ArH), 7.71 (s, 1 H, C=CH). 13C NMR (63 MHz, DMSO-d 6): δ = 16.5, 47.1, 56.7, 56.8, 57.2, 115.1 (2 C), 115.3 (2 C), 121.8, 127.4 (2 C), 130.0 (2 C), 130.1, 131.0, 131.7 (2 C), 131.8, 131.9 (2 C), 132.5, 143.0, 150.2, 160.1, 160.6, 168.1. IR: ν = 2840, 1698, 1646, 1610, 1585, 1513, 1497, 1467, 1423, 1403, 1380, 1331, 1295, 1248, 1171, 1162, 1092, 1072, 1041, 1030 cm–1. ESI-HRMS: m/z calcd for C27H27N2O3S2 [M + H]+: 491.1463; found: 491.1440. Compound 13: yellow solid (130 mg, 51%); mp 141–143 °C. 1H NMR (250 MHz, CDCl3): δ = 3.81 (s, 3 H, OCH3), 3.84 (s, 3 H, OCH3), 4.66 (s, 2 H, C=NCH2), 5.05 (s, 2 H, NCH2), 6.84–6.94 (m, 6 H, ArH), 7.29–7.55 (m, 8 H, ArH and C=CH), 7.78 (d, 2 H, J = 6.8 Hz, ArH). 13C NMR (63 MHz, CDCl3): δ = 45.5, 55.2, 55.3, 55.5, 108.3, 113.7 (2 C), 113.8 (2 C), 116.2, 118.3, 119.0, 124.3 (2 C), 128.5, 128.7 (2 C), 128.9 (2 C), 129.0, 129.6, 130.3, 130.4 (2 C), 131.4, 149.7, 156.9, 158.7, 159.1, 166.4. IR: ν = 2924, 2851, 1728, 1697, 1678, 1647, 1608, 1510, 1439, 1415, 1379, 1328, 1289, 1244, 1163, 1110, 1088, 1029 cm–1. ESI-HRMS: m/z calcd for C30H27N2O4S [M + H]+: 511.1685; found: 511.1694. Compound 21: yellow solid (52 mg, 29%); mp 68 °C. 1H NMR (250 MHz, CDCl3): δ = 0.94–1.01 (m, 6 H, 2 × CH3), 1.34–1.49 (m, 4 H, 2 × CH2), 1.63–1.74 (m, 4 H, 2 × CH2), 2.54 (s, 3 H, SCH3), 3.42 (t, 2 H, J = 6.8 Hz, C=NCH2), 3.87 (t, 2 H, J = 7.2 Hz, NCH2), 7.30 (d, 2 H, J = 8.5 Hz, Har), 7.47 (d, 2 H, J = 8.5 Hz, Har), 7.66 (s, 1 H, C=CH). 13C NMR (63 MHz, CDCl3): δ = 13.7, 13.9, 15.1, 20.0, 20.5, 29.5, 32.8, 42.8, 52.9, 120.9, 126.0 (2 C), 128.6, 130.2 (2 C), 130.6, 141.1, 147.3, 166.9. IR: ν = 2952, 2851, 2817, 1706, 1641, 1602, 1586, 1490, 1429, 1381, 1295, 1261, 1198, 1116, 1090, 1009 cm–1. ESI-HRMS: m/z calcd for C19H27N2OS2 [M + H]+: 363.1559; found: 363.1559