Download PDF
Synthesis 2014; 46(22): 3097-3102
DOI: 10.1055/s-0034-1378551
paper
© Georg Thieme Verlag Stuttgart · New York

Reactions of Dimethyl Acetylenedicarboxylate with 2,5-Dithiobiurea Derivatives

Alaa A. Hassan*
a   Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, A. R. Egypt   Fax: +20(86)236011   Email: alaahassan2001@mu.edu.eg
,
Nasr K. Mohamed
a   Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, A. R. Egypt   Fax: +20(86)236011   Email: alaahassan2001@mu.edu.eg
,
Maysa M. Makhlouf
a   Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, A. R. Egypt   Fax: +20(86)236011   Email: alaahassan2001@mu.edu.eg
,
Stefan Bräse
b   Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
,
Martin Nieger
c   Laboratory of Inorganic Chemistry, Department of Chemistry, University of Helsinki, P.O. Box 55 (A. I. Virtasen aukio I), 00014 Helsinki, Finland
› Author Affiliations
Further Information

Publication History

Received: 22 April 2014

Accepted after revision: 01 July 2014

Publication Date:
14 August 2014 (online)

    Permissions and Reprints All articles of this category


Abstract

Symmetrically and unsymmetrically N1,N2-disubstituted hydrazine-1,2-dicarbothioamides (2,5-dithiobiureas) react with dimethyl acetylenedicarboxylate in refluxing ethanol to give dimethyl 2,2′-[2,2′-(hydrazine-1,2-diylidene)bis(3-aryl/alkyl-4-oxothiazolidine-5,2-diylidene)diacetate and methyl 2-(2-{[5-(2-methoxy-2-oxoethylidene)-4-oxothiazolidin-2-ylidene]hydrazono}-4-oxothiazolidin-5-ylidene)acetate derivatives and N2,N5-disubstituted 1,3,4-thiadiazole-2,5-diamines. The structure of one product has been confirmed by a single-crystal X-ray structure analysis. A rationale for the formation of the products is presented.

Key words

dimethyl acetylenedicarboxylate - dithiobiurea derivatives - thiazolidinones - thiadiazoles

Supporting Information

    for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
  • Supporting Information
 

  • References

  • 1 Lewis JR. J. Nat. Prod. Rep. 2000; 17: 57
    CrossrefSearch in Google Scholar
  • 2 Jansen M, Rabe H, Strehle A, Dieler S, Debus F, Dannhardt G, Akabas MH, Lüddens H. J. Med. Chem. 2008; 51: 4430
    CrossrefSearch in Google Scholar
  • 3 Patel KN, Jadhav NC, Jagadhane PB, Telvekar VN. Synlett 2012; 23: 1970
    Thieme ConnectSearch in Google Scholar
  • 4 Chaudhari PS, Pathare SP, Akamanchi KG. J. Org. Chem. 2012; 77: 3716
    CrossrefSearch in Google Scholar
  • 5 Hassan AA, Mourad A.-FE, El-Shaieb KM, Abou-Zied AH, Döpp D. Heteroat. Chem. 2003; 14: 535
    CrossrefSearch in Google Scholar
  • 6 Hassan AA, Mourad A.-FE, El-Shaieb KM, Abou-Zied AH. Molecules 2005; 10: 822
    CrossrefSearch in Google Scholar
  • 7 Hassan AA, Mourad A.-FE, El-Shaieb KM, Abou-Zied AH. Z. Naturforsch., B 2004; 59: 910
    Search in Google Scholar
  • 8 Gruttadauria M, Lo Meo P, Noto R. Tetrahedron 2001; 57: 1819
    CrossrefSearch in Google Scholar
  • 9 Gruttadauria M, Aprile C, D’anna F, Lo Meo P, Riela S, Noto R. Tetrahedron 2001; 57: 6815
    CrossrefSearch in Google Scholar
  • 10 Padmavathi V, Radhalakshmi T, Mahesh K, Mohan AV. N. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2008; 47: 1707
    Search in Google Scholar
  • 11 Reddy CS, Rao DC, Yakub V, Nagaraj A. Acta Chim. Slov. 2010; 57: 798
    Search in Google Scholar
  • 12 Gantla C, Sarat M, Suresh Y, Harikrishana S, Shrivastava SP. Orient. J. Chem. 2009; 25: 211
    Search in Google Scholar
  • 13 Metwally MA, Fekri A, Nagy N, Amer FA. Am. J. Chem. 2012; 2: 277
    Search in Google Scholar
  • 14 Coulibaly WK, Paquin L, Bénié A, Bekro Y.-A, Durieux E, Meijer L, Le Guével R, Corlu A, Bazureau J.-P. Sci. Pharm. 2012; 80: 825
    CrossrefSearch in Google Scholar
  • 15 Abo-Bakr AM. Int. J. Sci. Eng. Res. 2013; 4: 1438 ; http://www.ijser.org/onlineResearchPaperViewer.aspx?Synthesis-and-evaluation-of-antimicrobial-activity-of-some-new-heterocyclic-compounds.pdf
    Search in Google Scholar
  • 16 Shrivastava SP, Seelam N, Rai R. E.-J. Chem. 2012; 9: 825 ; http://www.hindawi.com/journals/chem/
    Search in Google Scholar
  • 17 Alizadeh A, Noaparast Z, Sabahno H, Zohreh N. Helv. Chim. Acta. 2010; 93: 1401
    CrossrefSearch in Google Scholar
  • 19 Boschelli DH, Connor DT, Bornemeier DA, Dyer RD, Kennedy JA, Kuipers PJ, Okonkwo GC, Schrier DJ, Wright CD. J. Med. Chem. 1993; 36: 1802
    CrossrefPubMedSearch in Google Scholar
  • 20 Kumar D, Patel G, Chavers AK, Chang K.-H, Shan K. Eur. J. Med. Chem. 2011; 46: 3085
    CrossrefSearch in Google Scholar
  • 21 Tomita Y, Kabashima S, Okawara T, Yamasaki T, Furukawa M. J. Heterocycl. Chem. 1990; 27: 707
    CrossrefSearch in Google Scholar
  • 22 Yella R, Khatun N, Rout SK, Patel BK. Org. Biomol. Chem. 2011; 9: 3235
    CrossrefSearch in Google Scholar
  • 23 Kepe V, Požgan F, Golobič A, Polanc S, Kočevar M. J. Chem. Soc., Perkin Trans. 1 1998; 2813
  • 24 Mizrakh LT, Polanskaya LYu, Gvozdetskii AN, Vosil’ev AM, Ivanova TM, Lisina NI. S. Khim.-Farm. Zh. 1987; 21: 322 ; Chem. Abstr. 1988, 108, 21771r
    Search in Google Scholar
  • 25 Silberg A, Simiti I, Cosma N, Proinov I. Acad. Repub. Pop. Rom., Fil. Cluj, Stud. Cercet. Chim. 1957; 8: 315 ; Chem. Abstr. 1961, 55, 17626e
    Search in Google Scholar
  • 26 Bazavova IM, Dubenko RG, Shevchenko LI, Pel’kis PS. Ukr. Khim. Zh. (Russ. Ed.) 1980; 46: 286 ; Chem. Abstr. 1980, 93, 71237p
    Search in Google Scholar
  • 27 Udo E, Johannes D. DD 86815, 1972 ; Chem. Abstr. 1973, 78, 110637f.
  • 28 Raphael E, Joshua CP, Koshy L. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1989; 28: 635
    Search in Google Scholar
  • 29 Heinz E, Berscheid R. SOFW J. 1994; 120: 286 ; Chem. Abstr. 1996, 124, 55859W
    Search in Google Scholar
  • 30 Shen T.-Y, Clark RL, Pessolano AA. ZA 7503527, 1976 ; Chem. Abstr. 1977, 86, 72662r.
  • 31 Konher MV. Indian. J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1970; 8: 391
    Search in Google Scholar
  • 32 Sheldrick GM. Acta Crystallogr., Sect. A 2008; 64: 112
    CrossrefPubMedSearch in Google Scholar
  • 33 Crystallographic data (excluding structure factors) for the structure reported in this work have been deposited with Cambridge Crystallographic Data center as supplementary publication no. CCDC-995429. Copies of the data can be obtained free of charge on application to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033: e-mail: deposit@ccdc.cam.ac.uk].