Facile and selective synthesis of 4-methyl- and 4-phenylthiosemicarbazide (= N-methyl- and N-phenylhydrazinecarbothioamide) derivatives of benzil (= 1,2-Diphenylethane-1,2-dione)

Helvetica Chimica Acta

Volumn 90, Issue 11, 2007, Pages 2201-2216

  Calatayud, David G ^a   Escolar, Francisco J ^a   López Torres, Elena ^a   Mendiola, M Antonia ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

4-METHYLTHIOSEMICARBAZIDE; CYCLIC COMPOUND;

CONDENSATION; DERIVATIVES; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

HYDRAZINE DERIVATIVE; HYDROCHLORIC ACID; METHYL GROUP;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLIZATION; DILUTION; DRUG SYNTHESIS; MASS SPECTROMETRY; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 36549043542     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200790228     Document Type: Article

References (40)

1. D. X. West, A. E. Liberta, S. B. Padhye, R. C. Chikate, P. B. Sonawane, A. S. Kumbhar, R. G. Yeranda, Coord. Chem. Rev. 1993, 123, 49 and refs. cit. therein;
2. A. E. Liberta, D. X. West, Biometals 1992, 5, 121;
3. D. X. West, S. B. Padhye, P. B. Sonawane, Struct. Bonding 1991, 76, 1;
4. 'International Encyclopedia of Pharmacology and Therapeutics', Eds. J. G. Cory and A. H. Cory, Pergamon Press, New York, 1989;
5. R. Pedrido, M. R. Bermejo, M. J. Romero, M. Vázquez, A. M. González-Noya, M. Maneiro, M. J. Rodríguez, M. I. Fernández, Dalton Trans. 2005, 572;
6. I. H. Hall, K. G. Rajendran, D. X. West, A. E. Liberta, Anticancer Drugs 1993, 4, 231;
7. M. Belicchi-Ferrari, F. Bisceglie, C. Casoli, S. Durot, I. Morgenstern-Baradau, G. Pelosi, E. Piloti, S. Pinelli, P. Tarasconi, Med. Chem. 2005, 48, 1671;
8. H. Beraldo, D. Cambino, Mini-Rev. Med. Chem. 2004, 4, 31;
9. A. G. Quiroga, C. N. Ranninger, Coord. Chem. Rev. 2004, 248, 119;
10. N. C. Kasuga, K. Onodera, S. Nakano, K. Hayashi, K. Nomiya, J. Inorg. Biochem. 2006, 100, 1176.
11. A. R. Cowley, J. Davis, J. R. Dilworth, P. S. Donnelly, R. Dobson, A. Mightingale, J. M. Peach, B. Shore, D. Ker, L. Seymour, Chem Commun. 2005, 7, 845;
12. J. P. Holland, J. C. Green, J. R. Dilworth, Dalton Trans. 2006, 783;
13. A. R. Cowley, J. R. Dilworth, P. S. Donnelly, J. M. White, Inorg. Chem. 2006, 45, 496.
14. M. M. Reinoso García, W. Verboom, D. N. Reinhoudt, E. Malinowska, M. Pietrzak, D. Wojciechowska, Tetrahedron 2004, 60, 11299;
15. G. E. Tumambac, M. Rosencrance, C. Wolf, Tetrahedron 2004, 60, 11293;
16. S.-M. Cheung, W.-H. Chan, Tetrahedron 2006, 62, 8379.
17. a) L. Alsop, A. R. Cowley, J. R. Dilworth, P. S. Donnelly, J. M. Peach, J. T. Rider, Inorg. Chim. Acta 2005, 358, 2770;
18. b) M. Christlieb, J. R. Dilworth, Chem. - Eur. J. 2006, 12, 6194;
19. c) M. Christlieb, H. J. Claughton, A. R. Cowley, J. M. Heslop, J. R. Dilworth, Transition Met. Chem. 2006, 31, 88.
20. a) P. Souza, M. A. Mendiola, A. Arquero, V. Fernández, E. Gutiérrez-Puebla, C. Ruíz-Valero, Z. Naturforsch, B 1994, 49, 263;
21. b) A. Arquero, M. Cañadas, M. Martinez-Ripoll, M. A. Mendiola, A. Rodriguez, Tetrahedron 1998, 54, 11271;
22. c) M. A. Blanco, E. López-Torres, M. A. Mendiola, E. Brunet, M. T. Sevilla, Tetrahedron 2002, 58, 1525;
23. d) E. López-Torres, M. A. Mendiola, C. J. Pastor, B. Souto Pérez, Inorg. Chem. 2004, 43, 5222 and refs. cit. therein;
24. e) E. López-Torres, M. A. Mendiola, C. J. Pastor, Inorg. Chem. 2006, 45, 3103 and refs. cit. therein;
25. f) E. López-Torres, M. A. Mendiola, C. J. Pastor, Polyhedron 2006, 25, 1464.
26. M. J. Gismera, M. A. Mendiola, J. Rodríguez-Procopio, M. T. Sevilla, Anal. Chim. Acta 1999, 385, 143;
27. J. Ruipérez, M. A. Mendiola, M. T. Sevilla, J. Rodríguez-Procopio, L. Hernández, Electroanalysis 2002, 14, 532;
28. M. Colilla, M. A. Mendiola, J. R. Procopio, M. T. Sevilla, Electroanalysis 2005, 17, 933;
29. F. Zani, D. G. Calatayud, E. López-Torres, M. A. Mendiola, J. R. Procopio, 'EUROBIC 8 Conference book', ISBN 989-20-0305-5, Aveiro, Portugal, 2006, p. 153.
30. E. Franco, E. López-Torres, M. A. Mendiola, M. T. Sevilla, Polyhedron 2000, 19, 441.
31. E. Bermejo, A. Castiñeiras, D. X. West, J. Mol. Struct. 2003, 650, 93.
32. A. Castiñeiras, E. Bermejo, D. X. West, J. Mol. Struct. 1999, 478, 73.
33. A. L. Spek, PLATON, The University of Utrecht, Utrecht, 2004.
34. E. Bermejo, A. Castiñeiras, R. Dominguez, R. Carballo, C. Maiche-Mössmer, J. Strähle, D. X. West, Z. Anorg. Allg. Chem. 1999, 625, 961.
35. E. Sutton, 'Tables of Interatomic Distances and Configuration in Molecules and Ions (Suplement)', The Chemical Society, London, 1965.
36. G. M. Sheldrick, SADABS version 2.03, Program for Empirical Absorption Corrections, Universität Göttingen, Göttingen, 1997-2001.
37. G. M. Sheldrick, SAINT+NT (version 6.04) SAX, Area-Detector Integration Program, Bruker AXS, Madison, WI, 1997-2001.
38. Bruker AXS SHELXTL (version 6.10), Structure Determination Package, Bruker AXS, Madison, WI, 2000.
39. G. M. Sheldrick, SHELXS-90, Program for Structure Solution: Direct Methods, Acta Crystallogr. Sect. A 1990, 46, 467.
40. G. M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, Universität Göttingen, Göttingen, 1997.