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Synthesis of 5-acetyl-4,6-dimethyl-1,2,3,4-tetrahydropyrimidine-2-thione and structural characterization of its polymorphs and complexes with 12-group metal iodides

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Abstract

A novel cyclic thiourea, 5-acetyl-4,6-dimethyl-1,2,3,4-tetrahydropyrimidine-2-thione (L), was synthesized by the reaction of N-(1-tosylethyl)thiourea with potassium enolate of acetylacetone followed by acid-catalyzed dehydration of the obtained 5-acetyl-4-hydroxy-4,6-dimethylhexahydropyrimidine-2-thione. Its polymorphs and complexes with zinc, cadmium, and mercury iodides were studied by X-ray diffraction. Two polymorphs of 5-acetyl-4,6-dimethyl-1,2,3,4-tetrahydropyrimidine-2-thione differ in ring conformation and packing manner. In the monomeric cadmium complex [CdL2I2], the central atom is tetrahedrally coordinated in the standard manner by iodine and thiocarbonyl S atoms, while in the dimeric mercury complex [Hg2L2I4], every mercury atom is coordinated by two bridging I atoms, one terminal I atom and one thiocarbonyl S atom of the ligand. In the polymeric zinc complex [ZnLI2], the zinc tetrahedra are linked by the bidentate bridging 5-acetyl-4,6-dimethyl-1,2,3,4-tetrahydropyrimidine-2-thione molecules through thiocarbonyl S atom and acetyl O atom.

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References

  1. Atwal KS, Swanson BN, Unger SE, Floyd DM, Moreland S, Hedberg A, O’Reilly BC (1991) J Med Chem 34:806

    Article  CAS  Google Scholar 

  2. Grover GJ, Dzwonczyk S, McMullen DM, Normandin DE, Parham CS, Sleph PG, Moreland S (1995) J Cardiovasc Pharmacol 26:289

    Article  CAS  Google Scholar 

  3. Haggarty SJ, Mayer TU, Miyamoto DT, Fathi R, King RW, Mitchison TJ, Schreiber SL (2000) Chem Biol 7:275

    Article  CAS  Google Scholar 

  4. Nagarathnam D, Miao SW, Lagu B, Chiu G, Fang J, Dhar TGM, Zhang J, Tyagarajan S, Marzabadi MR, Zhang FQ, Wong WC, Sun WY, Tian D, Wetzel JM, Forray C, Chang RSL, Broten TP, Ransom RW, Schorn TW, Chen TB, O’Malley S, Kling P, Schneck K, Benedesky R, Harrell CM, Vyas KP, Gluchowski C (1999) J Med Chem 42:4764

    Article  CAS  Google Scholar 

  5. Kappe CO (2000) Eur J Med Chem Chim Ther 35:1043

    Article  CAS  Google Scholar 

  6. Rovnyak GC, Kimball SD, Beyer B, Cucinotta G, Di Marco JD, Gougoutas J, Hedberg A, Malley M, McCarthy JP, Zhang R, Moreland S (1995) J Med Chem 38:119

    Article  CAS  Google Scholar 

  7. Shishkin OV, Solomovich EV, Vakula VM, Yaremenko FG (1997) Russ Chem Bull 1838

  8. Kappe CO, Fabian WMF, Semones MA (1997) Tetrahedron 53:2803

    Article  CAS  Google Scholar 

  9. Fabian WMF, Semones MA, Kappe CO (1998) J Mol Struct THEOCHEM 432:219

    Article  CAS  Google Scholar 

  10. Kappe CO, Shishkin OV, Uray G, Verdino P (2000) Tetrahedron 56:1859

    Article  CAS  Google Scholar 

  11. Uray G, Verdino P, Belaj F, Kappe CO, Fabian WMF (2001) J Org Chem 66:6685

    Article  CAS  Google Scholar 

  12. Shutalev AD, Kuksa VA (1995) Chem Heterocycl Compd 31:86

    Article  Google Scholar 

  13. Shutalev AD (1997) Chem Heterocycl Compd 33:1469

    Article  CAS  Google Scholar 

  14. Shutalev AD, Kishko EA, Sivova NV, Kuznetsov AYu (1998) Molecules 3:100

    Article  CAS  Google Scholar 

  15. Field L, Clark RD (1958) Org syntheses, vol 38. John Wiley and Sons, New York, p 62

    Google Scholar 

  16. Sheldrick GM (2008) Acta Crystallogr A64:112

    CAS  Google Scholar 

  17. Zlokazov VB, Chernyshev VV (1992) J Appl Cryst 25:447

    Article  Google Scholar 

  18. Albov DV, Davydov DV, Chernyshov VV (2004) Acta Crystallogr E60:m1193

    CAS  Google Scholar 

  19. Favre-Nicolin V, Cerny R (2000–2008) University of Geneva, http://objcryst.sourceforge.net

  20. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03, Revision E.01. Gaussian, Wallingford, CT

    Google Scholar 

  21. Popovic Z, Pavlovic G, Matkovic-Calogovic D, Soldin Z, Rajic M, Vikic-Topic D, Kovacek D (2000) Inorg Chim Acta 306:142

    Article  CAS  Google Scholar 

  22. Matcovic-Calogovic D, Popovic Z, Pavlovic G, Soldin Z, Giester G (2001) Acta Crystallogr C57:409

    Google Scholar 

  23. Razak IA, Usman A, Fun H-K, Yamin BM, Keat GW (2002) Acta Crystallogr C58:m31

    CAS  Google Scholar 

  24. Lundberg D, Eriksson L (2006) Acta Crystallogr E60:m400

    Google Scholar 

  25. Zamilatskov IA, Savinkina EV, Al’bov DV (2007) Rus J Coord Chem 33:396

    Article  CAS  Google Scholar 

  26. Laifa EA, Bendjeddou L, Boudraa N, Dahaoui S, Lecomte C (2009) Acta Crystallogr E65:m1080

    CAS  Google Scholar 

  27. Vallat O, Neels A, Stoeckli-Evans H (2003) J Chem Cryst 33:39

    Article  CAS  Google Scholar 

  28. Cui D-J, Zeng X-S, Leng X-B, Xu F-B, Zhang Z-Z (2003) Acta Crystallogr E59:o868

    CAS  Google Scholar 

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Acknowledgment

The support of part of this work by the President Grant MK-3576.2009.3 is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Organic Chemistry, Moscow State Academy of Fine Chemical Technology, 86 Vernadsky Prospect, Moscow, Russia, 119571

    Anatoly D. Shutalev

  2. Department of Inorganic Chemistry, Moscow State Academy of Fine Chemical Technology, 86 Vernadsky Prospect, Moscow, Russia, 119571

    Elena V. Savinkina & Evgueny A. Buravlev

  3. Department of Chemistry, Moscow State University, Vorob’evy gory, Moscow, Russia, 119992

    Dmitry V. Albov

  4. Frumkin Institute of Physical Chemistry and Electrochemistry, 31 Leninsky Prospect, Moscow, Russia, 119991

    Ilia A. Zamilatskov

Authors
  1. Anatoly D. Shutalev
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  2. Elena V. Savinkina
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  3. Dmitry V. Albov
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  4. Ilia A. Zamilatskov
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  5. Evgueny A. Buravlev
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Correspondence to Anatoly D. Shutalev.

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Shutalev, A.D., Savinkina, E.V., Albov, D.V. et al. Synthesis of 5-acetyl-4,6-dimethyl-1,2,3,4-tetrahydropyrimidine-2-thione and structural characterization of its polymorphs and complexes with 12-group metal iodides. Struct Chem 22, 849–855 (2011). https://doi.org/10.1007/s11224-011-9770-7

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  • DOI: https://doi.org/10.1007/s11224-011-9770-7

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