A study of the Willgerodt-Kindler reaction to obtain thioamides and α-ketothioamides under solvent-less conditions

Canadian Journal of Chemistry

Volumn 90, Issue 7, 2012, Pages 567-573

  Valdez Rojas, José Ernesto ^a   Ríos Guerra, Hulme ^a   Ramírez Sánchez, Alma Leticia ^a   García González, Guadalupe ^a   Álvarez Toledano, Cecilio ^b   López Cortés, José Guadalupe ^b   Toscano, Rubén A ^b   Penieres Carrillo, José Guillermo ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

ketothioamides; IR energy; Noncatalyst; Solvent less conditions; Willgerodt Kindler modification

Indexed keywords

IR ENERGY; NONCATALYST; SOLVENT FREE; SOLVENT-LESS CONDITIONS; THIOAMIDES; WILLGERODT-KINDLER MODIFICATION;

CHEMISTRY;

SOLVENTS;

EID: 84863823107     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v2012-030     Document Type: Article

References (51)

1. Freerksen, E. Synergistic Therapeutic Composition for the Treatment of Mycobacterioses. US Patent 4,005,207, January 25, 1977.
2. Tsung-Ying, S; Dorn, K. P, Jr.; Witzel, B. E. Substituted Biphenyl Acetic Acid Derivatives. US Patent 3,624,142, November 30, 1971.
3. a Banala S. Süssmuth R. D. ChemBioChem 2010, 11 (10), 1335. 10.1002/cbic.201000266
4. b Kramer, W.; Draber, W.; Timmler, H.; Forster, H. Process for the Preparation of α-Oxothiodimethylamide Compounds. US Patent 4,028,409, June 7, 1977
5. c Fusseneger M. Weber W. Schoenmakers R. US Patent Application. 2011, US2011 (0053880), A1.
6. a Searle, R. J. G.; Boyce, C. B. C.; Bay, H. Thioamide Pesticides. US Patent 4,096,275, June 20, 1978
7. b Fauss, R.; Findeisen, K.; Becker, B.; Hamman, I.; Homeyer, B. Pesticidal Novel Substituted Hydroxymalonic Acid Amide-Thiomides. US Patent 4,581,375, April 8, 1986.
8. a Meltzer R. I. Lewis A. D. King J. A. J. Am. Chem. Soc. 1955, 77 (15), 4062. 10.1021/ja01620a029
9. b Wang F. Langley R. Gulten G. Dover L. G. Besra G. S. Jacobs W. R. Sacchettini J. C. J. Exp. Med. 2007, 204 (1), 73. 10.1084/jem.20062100 (Pubitemid 46148758)
10. a Stiller E. T. Diassi P. A. Gerschutz D. Meikle D. Moetz J. Principe P. A. Levine S. D. J. Med. Chem. 1972, 15 (10), 1029. 10.1021/jm00280a009
11. b Gala D. Stamford A. Jenkins J. Kugelman M. Org. Process Res. Dev. 1997, 1 (2), 163. 10.1021/op960035c (Pubitemid 127071017)
12. Harrowven D. C. Lucas M. C. Howes P. D. Tetrahedron Lett. 1999, 40 (23), 4443. 10.1016/S0040-4039(99)00768-6 (Pubitemid 29251468)
13. a Koketsu M. Ishihara H. Curr. Org. Synth. 2007, 4 (1), 15. 10.2174/157017907779981615
14. b Metzner, P. Thiocarbonyl Compounds as Specific Tools for Organic Synthesis. In Topics in Current Chemistry; Organosulfur Chemistry I, Vol. 204; Springer: New York, 1999; pp 127-181.
15. Willgerodt C. Ber. Dtsch. Chem. Ges. 1887, 20 (2), 2467. 10.1002/cber.18870200278
16. Dauben W. Rogan J. J. Am. Chem. Soc. 1956, 78 (16), 4135. 10.1021/ja01597a075
17. Harris T. W. Smith H. E. Mobley P. L. Manier D. H. Sulser F. J. Med. Chem. 1982, 25 (7), 855. 10.1021/jm00349a018 (Pubitemid 12056969)
18. Harrowven D. C. Lucas M. C. Tetrahedron 1999, 55 (4), 1187. 10.1016/S0040-4020(98)01096-5 (Pubitemid 29045630)
19. Liu W. W. Zhao Y. Q. Xu R. B. Tang L. J. Hu H. W. Chin. J. Chem. 2006, 24 (10), 1472. 10.1002/cjoc.200690278
20. Asinger F. Schåfer W. Baumgarte G. Müting P. F. Liebigs Ann. Chem. 1963, 661 (1), 95. 10.1002/jlac.19636610108
21. Asinger F. Saus A. Offermanns H. Hahn H. D. Justus Liebigs Ann. Chem. 1966, 691 (1), 92. 10.1002/jlac.19666910114
22. Moghaddam F. H. Mirjafary Z. Saeidian H. Javan M. J. Synlett 2008, 2008 (6), 892. 10.1055/s-2008-1042925 (Pubitemid 351522703)
23. a Merz, W. Process for the Preparation of Alkali Metal Salts of 3,3-Dimethyl-2-oxo-butyric Acid. US Patent 4,113,767, September 12, 1978
24. b Merz, W. Process for the Preparation of 6-tert-Butyl-3-mercapto-4- amino-1,2,4-triazin-5(4 H)-one. US Patent 4,151,355, April 24, 1979.
25. Adiwidjaja G. Gunther H. Voss J. Angew. Chem. Int. Ed. Engl. 1980, 19 (7), 563. 10.1002/anie.198005631
26. Murata S. Suzuki K. Miura M. Nomura M. J. Chem. Soc., Perkin Trans. 1 1990, (2): 361. 10.1039/p19900000361
27. Raucher S. Klein P. J. Org. Chem. 1981, 46 (17), 3558. 10.1021/jo00330a041
28. a Nooshabadi M. Aghapoor K. Darabi H. R. Mojtahedi M. M. Tetrahedron Lett. 1999, 40 (42), 7549. 10.1016/S0040-4039(99)01600-7 (Pubitemid 29481212)
29. b Olsson R. Hansen H. C. Andersson C. M. Tetrahedron Lett. 2000, 41 (41), 7947. 10.1016/S0040-4039(00)01360-5
30. c Aghapoor K. Darabi H. Tabar-Heydar K. Nakhshab L. Sulfur Lett. 2002, 25 (6), 259. 10.1080/02786110215846
31. d Zbruyev O. I. Stiasni N. Kappe C. O. J. Comb. Chem. 2003, 5 (2), 145. 10.1021/cc0200538 (Pubitemid 37123506)
32. e Darabi H. R. Aghapoor K. Tajbakhsh M. Tetrahedron Lett. 2004, 45, 4617
33. f Poupaert J. H. Duarte S. Colacino E. Depreux P. McCurdy C. R. Lambert D. L. Phosphorus Sulfur Silicon Relat. Elem. 2004, 179 (10), 1959. 10.1080/10426500490466995 (Pubitemid 39456896)
34. g Holt J. J. Calitree B. D. Vincek J. Gannon M. K. Detty M. R. J. Org. Chem. 2007, 72 (7), 2690. 10.1021/jo070086f (Pubitemid 46536208)
35. h Darabi H. R. Aghapoor K. Balavar Y. Mobedi E. Farhangian H. Mohsenzadeh F. Z. Naturforsch. 2008, 63b, 993.
36. Miranda R. Noguez O. Velasco B. Arroyo G. Penieres G. Martínez J. O. Delgado F. Educ. Quim. 2009, 20 (4), 421.
37. Camarena R. Cano A. C. Delgado F. Zuiga N. Álvarez C. García O. Tetrahedron Lett. 1993, 34 (43), 6857. 10.1016/S0040-4039(00) 91813-6
38. Salmón M. Osnaya R. Gómez L. Arroyo G. Delgado F. Miranda R. J. Mex. Chem. Soc. 2001, 45, 206.
39. a Delgado F. Tamariz J. Zepeda G. Landa M. Miranda R. García J. Synth. Commun. 1995, 25 (5), 753. 10.1080/00397919508011413
40. b Obrador E. Castro M. Tamaríz J. Zepeda G. Miranda R. Delgado F. Synth. Commun. 1998, 28 (24), 4649. 10.1080/00397919808004530
41. c Alcerreca G. Sanabria R. Miranda R. Arroyo G. Tamariz J. Delgado F. Synth. Commun. 2000, 30 (7), 1295. 10.1080/00397910008087151
42. Penieres-Carrillo G. García-Estrada J. G. Gutiérrez- Ramírez J. L. Álvarez-Toledano C. Green Chem. 2003, 5 (3), 337. 10.1039/b211011c
43. Noguez M. O. Marcelino V. Rodríguez H. Martín O. Martínez J. O. Arroyo G. A. Pérez F. J. Suárez M. Miranda R. Int. J. Mol. Sci. 2011, 12 (4), 2641. 10.3390/ijms12042641
44. Penieres G. Aceves J. M. Flores A. Mendoza G. Garcia O. Álvarez C. Heterocycl. Commun. 1997, 3 (6), 507. 10.1515/HC.1997.3.6.507
45. McNally, J. P.; Leong, V. S.; Cooper, N. J. Cannula Techniques for the Manipulation of Air-Sensitive Materials. In Experimental Organometallic Chemistry; Wayda, A.L., Darensbourg, M.Y., Eds.; ACS Symposium Series 357, Washington, DC, 1987; Chapter 2, pp 6-33.
46. a Altomare A. Cascarano G. Giacovazzo C. Guagliardi A. Burla M. C. Polidori G. Canalli M. J. Appl. Cryst. 1994, 27, 435
47. b Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
48. a Lundstedt T. Thoren P. Carlson R. Norin T. Mörch L. Acta Chem. Scand. B 1984, 38b, 717. 10.3891/acta.chem.scand.38b-0717
49. b Rais A. Ankati H. Biehl E. J. Heterocycl. Chem. 2009, 46 (4), 599. 10.1002/jhet.88
50. Carmack M. Behforouz M. Berchtold G. A. Berkowitz S. M. Wiesler D. Barone R. J. Heterocycl. Chem. 1989, 26 (5), 1305. 10.1002/jhet.5570260517
51. Darabi H. R. Aghapoor K. Nakhshab L. Z. Naturforsch. 2004, 59b, 601.