Preparation of mono-, di-, and trisubstituted ureas by carbonylation of aliphatic amines with S,S-dimethyl dithiocarbonate

Synthesis

Volumn , Issue 22, 2007, Pages 3497-3506

  Artuso, Emma ^a   Degani, Iacopo ^a   Fochi, Rita ^a   Magistris, Claudio ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

Amines; Carbonylation; Dithiocarbonates; Thiocarbamates; Ureas

Indexed keywords

DIMETHYL DITHIOCARBONATE (DMDTC); DITHIOCARBONATES; PHOSGENE; THIOCARBAMATES;

AMINES; AMMONIA; CARBONYLATION; REACTION KINETICS;

UREA;

AMINE; BUTYLUREA; DITHIOCARBONIC ACID DIMETHYL ESTER; ETHYLUREA; METHYLUREA; N BENZYL N' BUTYLUREA; N BENZYL N' HEXYLUREA; N BENZYL N' METHYLUREA; N BENZYLUREA; N CYCLOHEXYL N' METHYLUREA; N CYCLOHEXYLUREA; N ETHYL N' METHYLUREA; N HEXYLUREA; N,N BIBUTYL N' METHYLUREA; N,N DIETHYL N' METHYLUREA; N,N' BIS(4 AMINOBENZYL)UREA; N,N' BIS(4 CHLOROBENZYL)UREA; N,N' BIS(4 METHYLBENZYL)UREA; N,N' DI(SEC BUTYL)UREA; N,N' DIALLYLUREA; N,N' DIBENZYLUREA; N,N' DIBUTYLUREA; N,N' DICYCLOHEXYLUREA; N,N' DIDECYLUREA; N,N' DIETHYLUREA; N,N' DIHEXYLUREA; N,N' DIISOBUTYLUREA; N,N' DIMETHYUREA; THIOCARBAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; CARBONYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; SYNTHESIS;

EID: 36749005584     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990813     Document Type: Article

References (78)

1. For reviews on ureas, see: (a) Sartori, G.; Maggi, R. In Science of Synthesis, Vol. 18; Knight, J. G., Ed.; Thieme Verlag: Stuttgart, 2005, 665-758.
2. (b) Bigi, F.; Maggi, R.; Sartori, G. Green Chem. 2000, 2, 140.
3. (c) Tafesh, A. M.; Weiguny, J. Chem. Rev. 1996, 96, 2035.
4. (d) Petersen, H. In Ullmann's Encyclopedia of Industrial Chemistry, 5th ed., Vol. A27; Elvers, B.; Hawkins, S., Eds.; VCH: Weinheim, 1996, 355-365.
5. (e) Vishnyakova, T. P.; Golubeva, I. A.; Glebova, E. V. Russ. Chem. Rev. 1985, 54, 249.
6. (f) Petersen, U. In Houben-Weyl, 4th ed., Vol. E4; Hagemann, H., Ed.; Thieme Verlag: Stuttgart, 1983, 334-367; and references cited therein.
7. (g) Melnikov, N. N. In Chemistry of Pesticides; Gunther, F. A.; Gunther, J. D., Eds.; Springer-Verlag: Berlin, 1971, 225-239.
8. For a plentiful recent literature (until 2003) on the synthesis and applications of substituted ureas see: Gabriele, B.; Salerno, G.; Mancuso, R.; Costa, M. J. Org. Chem. 2004, 69, 4741; and references cited therein.
9. Some recent references (after 2003) on new applications of substituted ureas: (a) Martinez Gil, A.; Medina Padilla, M.; Castro Morera, A.; Alonso Cascon, M.; Martin Aparicio, E.; Fuertes Huerta, A.; Navarro Rico, M. L.; Perez Puerto, M. J. Neuropharma S. A., Spain, EP 1749523, 2007; Chem. Abstr. 2007, 146, 206112.
10. (b) Bhalay, G.; Dunstan, A.; Glen, A.; Howe, T. J.; McCarthy, C. Novartis AG Switzerland, Novartis Pharma GmbH, WO 015852, 2006; Chem. Abstr. 2006, 144, 232805.
11. (c) Dasseux, J.-L. H.; Oniciu, D. C. Esperion Therapeutics Inc. USA, WO 068420, 2005; Chem. Abstr. 2005, 143, 172557.
12. (d) Carruthers, N. I.; Shah, C. R.; Swanson, D. M. Janssen Pharmaceutica, N. V., Belgium, WO 014580, 2005; Chem. Abstr. 2005, 142, 240468.
13. (e) Defossa, E.; Kadereit, D.; Klabunde, T.; Burger, H.-J.; Herling, A.; Wendt, K.-U.; Von Roedern, E.; Schoenafinger, K.; Enhsen, A. Aventis Pharma Deutschland GmbH, Germany, WO 065356, 2004; Chem. Abstr. 2004, 141, 173980.
14. Some recent references (after 2003) on the use of monoalkyl-, dialkyl-, and trialkylureas in organic synthesis: (a) Fritz, J. A.; Nakhla, J. S.; Wolfe, J. P. Org. Lett. 2006, 8, 2531.
15. (b) Sigachev, A. S.; Kravchenko, A. N.; Gazieva, G. A.; Belyakov, P. A.; Kolotyrkina, N. G.; Lebedev, O. V.; Makhova, N. N.; Lyssenko, K. A. J. Heterocycl. Chem. 2006, 43, 1295.
16. (c) Gel'mbol'dt, V. O.; Koroeva, L. V.; Filinchuk Ya, E. Russ. J. Coord. Chem. 2005, 31, 775.
17. (d) Natarajan, A.; Guo, Y.; Arthanari, H.; Wagner, G.; Halperin, J. A.; Chorev, M. J. Org. Chem. 2005, 70, 6362.
18. (e) Hansen, A. L.; Skrydstrup, T. J. Org. Chem. 2005, 70, 5997.
19. (f) Kravchenko, A. N.; Sigachev, A. S.; Maksareva, E. Y.; Gazieva, G. A.; Trunova, N. S.; Lozhkin, B. V.; Pivina, T. S.; Il'in, M. M.; Lyssenko, K. A.; Nelyubina, Y. V.; Davankov, V. A.; Lebedev, O. V.; Makhova, N. N.; Tartakovsky, V. A. Russ. Chem. Bull. 2005, 54, 691.
20. (g) Zhou, X.; Chen, Y.; Liu, B. Faming Zhuanli Shenqing Gongkai Shuomingshu, CN 1515540 A, 2004;
21. Chem. Abstr. 2005, 143, 77851.
22. Some recent references (after 2003) on the synthesis of monoalkyl-, dialkyl-, and trialkylureas: (a) Peng, X.; Li, F.; Xia, C. Synlett 2006, 1161; and references cited therein.
23. (b) Mizuno, T.; Mihara, M.; Iwai, T.; Ito, T.; Ishino, Y. Synthesis 2006, 2825; and references cited therein.
24. (c) Zhu, B.; Angelici, R. J. J. Am. Chem. Soc. 2006, 128, 14460.
25. (d) Orito, K.; Miyazawa, M.; Nakamura, T.; Horibata, A.; Ushito, H.; Nagasaki, H.; Yuguchi, M.; Yamashita, S.; Yamazaki, T.; Tokuda, M. J. Org. Chem. 2006, 71, 5951; and references cited therein.
26. (e) Fan, X.; Rui, B.; Yan, L.; Li, C. Faming Zhuanli Shenqing Gongkai Shuomingshu, CN 1827594 A, 2006; Chem. Abstr. 2006, 145, 397096.
27. (f) Wang, C.; Li, Y.; Du, M.; Xu, S.; Zheng, C.; Wang, C.; Yang, X.; Shi, L.; Wang, W. Faming Zhuanli Shenqing Gongkai Shuomingshu, CN 1740140 A, 2006;
28. Chem. Abstr. 2006, 145, 10086.
29. (g) Li, Z.; Wang, Z.-Y.; Zhu, W.; Xing, Y.-L.; Zhao, Y.-L. Synth. Commun. 2005, 35, 2325.
30. (h) Nishiyama, Y.; Kawamatsu, H.; Sonoda, N. J. Org. Chem. 2005, 70, 2551.
31. (i) Perveen, S.; Abdul Hai, S. M.; Khan, R. A.; Khan, K. M.; Afza, N.; Sarfaraz, T. B. Synth. Commun. 2005, 35, 1663.
32. (j) Enquist, P.-A.; Nilsson, P.; Edin, J.; Larhed, M. Tetrahedron Lett. 2005, 46, 3335.
33. (k) Fujita, S.; Bhanage, B. M.; Kanamaru, H.; Arai, M. J. Mol. Catal. A: Chem. 2005, 230, 43; and references cited therein.
34. (l) Pourali, A. R. Monatsh. Chem. 2005, 136, 733.
35. (m) Grzyb, J. A.; Shen, M.; Yoshina-Ishii, C.; Chi, W.; Brown, R. S.; Batey, R. A. Tetrahedron 2005, 61, 7153.
36. (n) Yang, C. Faming Zhuanli Shenqing Gongkai Shuomingshu, CN 1660795 A, 2005;
37. Chem. Abstr. 2006, 144, 469979.
38. (o) Hiwatari, K.; Kayaki, Y.; Okita, K.; Ukai, T.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2004, 77, 2237.
39. (p) Zhang, Q.; Shi, F.; Deng, Y. Cuihua Xuebao 2004, 25, 607;
40. Chem. Abstr. 2005, 142, 373529.
41. (q) Fujita, S.; Bhanage, B. M.; Arai, M. Chem. Lett. 2004, 742;
42. Chem. Abstr. 2004, 141, 156829.
43. (r) Qian, W. X.; Ju, F. Y.; Zhang, Y. M.; Bao, W. L. Chin. Chem. Lett. 2004, 15, 1269;
44. Chem. Abstr. 2005, 142, 155314.
45. (s) Porwanski, S.; Menuel, S.; Marsura, X.; Marsura, A. Tetrahedron Lett. 2004, 45, 5027.
46. Degani, I.; Fochi, R.; Regondi, V. Synthesis 1981, 149.
47. Oxon Italia S.p.A. (Italy).
48. (a) Degani, I.; Fochi, R.; Regondi, V. CNR, Italy, Eur. Pat. Appl. 63327, 1982; Chem. Abstr. 1983, 98: 160238.
49. (b) Degani, I.; Fochi, R.; Regondi, V. Synthesis 1983, 630.
50. (c) Degani, I.; Fochi, R.; Regondi, V. Synthesis 1986, 1070.
51. (d) Degani, I.; Fochi, R.; Regondi, V. CNR, Italy, IT 1173436, 1987.
52. Cadamuro, S.; Degani, I.; Fochi, R.; Regondi, V. Chem. Ind. (London) 1986, 671.
53. (a) Barbero, M.; Degani, I.; Fochi, R.; Regondi, V. CNR, Italy, Eur. Pat. Appl. 234249, 1987; Chem. Abstr. 1988, 108, 23697.
54. (b) Barbero, M.; Cadamuro, S.; Degani, I.; Fochi, R.; Regondi, V. Synthesis 1989, 857.
55. Leung, M.-kit; Lai, J.-L.; Lau, K.-H.; Yu, H.-hua.; Hsiao, H.-J. J. Org. Chem. 1996, 61, 4175.
56. IT patent pending: Carvoli, G.; Degani, I.; Pallucca, E.; Fochi, R.; Serri, A. M.; Cadamuro, S.; Gazzetto, S.; Migliaccio, M. Oxon Italia S.p.A., Italy, patent request No. MI 2004A 002402, (16.12.2004) 2004.
57. Artuso, E.; Carvoli, G.; Degani, I.; Fochi, R.; Magistris, C. Synthesis 2007, 1096.
58. For example, for toxicity of phosgene, see: (a) Sax, N. I. In Dangerous Properties of Industrial Materials; Van Nostrand Reinhold Company: New York, 1984, 2210-2211.
59. (b) Senet, J.-P. (Groupe SNPE) In The Recent Advance in Phosgene Chemistry, Vol. 1; GPA: Nanterre, 1997, 10-11.
60. (c) Cotarca, L.; Eckert, H. In Phosgenations - A Handbook; Wiley-VCH: Weinheim, 2003, 9.
61. Details are reported in an IT patent pending: Carvoli, G.; Degani, I.; Pallucca, E.; Fochi, R.; Gazzetto, S.; Artuso, E.; Lazzaroni, M.; Cadamuro, S. Oxon Italia S.p.A., Italy, patent request No. MI 2005A 001284, (07.07.2005) 2005.
62. Dictionary of Organic Compounds on CD-ROM; Chapman & Hall, Electronic Publishing Division: London, 2007, Version 15.1 [CD ROM].
63. (a) Atanassova, I. A.; Petrov, J. S.; Mollov, N. M. Synth. Commun. 1989, 19, 147.
64. (b) Hayashi, T.; Kuyama, M. Nat. Sci. Rep. Ochanomizu Univ. (Tokyo) 1951, 2, 79;
65. Chem. Abstr. 1954, 48, 1274b.
66. Bakibaev, A. A. Russ. J. Org. Chem. 1994, 30, 1772.
67. Troyanskii, E. A.; Ioffe, V. A.; Mizintsev, V. V.; Nikishin, G. I. Bull. Acad. Sci. USSR 1984, 33, 1661.
68. Lutsenko, V. V.; Blyum, R. A.; Knunyants, I. L. J. Chem. Org. USSR 1971, 7, 1182.
69. Martinelli, L. C.; DeWitt Blauton, C.; Whidby, J. F. J. Am. Chem. Soc. 1971, 93, 5111.
70. Kim, H. O.; Ji, X.; Melman, N.; Olah, M. E.; Stiles, G. L.; Jacobson, K. A. J. Med. Chem. 1994, 37, 3373.
71. Wiloth, F.; Schindler, E. Chem. Ber. 1970, 103, 757.
72. Nowick, J. S.; Abdi, M.; Bellamo, K. A.; Love, J. A.; Martinez, E. J.; Noronha, G.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 89.
73. Spectral Data Base for Organic Compounds SDBS (National Institute of Advanced Industrial Science and Technology). SDBS Web: http://www.aist.go.jp/ RIODB/SDBS.
74. McCusker, J. E.; Main, A. D.; Johnson, K. S.; Grasso, C. A.; McElwee-White, L. J. Org. Chem. 2000, 65, 5216.
75. (a) Kochansky, J. P.; Feldmesser, J. J. Nematol. 1989, 21, 158.
76. (b) Kochansky, J. P.; Feldmesser, J. J. Econ. Entomol. 1985, 78, 599.
77. Rouzer, C. A.; Sabourin, M.; Skinner, T. L.; Thompson, E. J.; Wood, T. O.; Chmurny, G. N.; Klose, J. R.; Roman, J. M.; Smith, R. H.; Michejda, C. J. Chem. Res. Toxicol. 1996, 9, 172.
78. Pallucca, E.; Degani, I.; Serri, A. M.; Fochi, R.; Gazzetto, S.; Fenoglio, C.; Ornati, C.; Migliaccio, M.; Cadamuro, S.; Carvoli, G. Oxon Italia S.p.A., Italy, EP 1334965, 2003; Chem. Abstr. 2003, 139, 164529.