Reaction of aromatic diamines with diphenylcarbonate catalyzed by phosphorous acids: A new clean synthetic route to mono- and dicarbamates

Tetrahedron

Volumn 54, Issue 46, 1998, Pages 14145-14156

  Aresta, Michele ^a,b   Dibenedetto, Angela ^a,b   Quaranta, Eugenio ^a,b  

^a UNIVERSITY OF BARI   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2,4 DIAMINOTOLUENE; AROMATIC COMPOUND; DIAMINE; PHOSPHORUS ACID DERIVATIVE;

ARTICLE; CARBOXYLATION; CATALYSIS; DRUG SYNTHESIS; ESTERIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0032512092     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00873-4     Document Type: Article

References (45)

1. 1. (a) Barthelemy, J. Lyon Pharm. 1986, 37(6), 297.
2. (b) Tai-Teh Wu; Huang, J.; Arrington, N.D.; Dill, G.M. J. Agric. Food Chem. 1987, 35, 817.
3. (c) Kato, T.; Suzuki, K.; Takahashi, J.; Kamoshita, K. J. Pesticide Sci. 1984, 9, 489.
4. (d) Picardi, P. La Chimica e l'Industria 1986, 68 (11), 108.
5. (e) Rivetti, F.; Romano, U.; Sasselli, M. U.S. Pat. 4514339, 1985.
6. 2. Babad, H.; Zeiler, A.G. Chem. Rev. 1973, 73, 75.
7. 3. (a) Aresta, M.; Quaranta, E. ChemTech, 1997, 27(3), 32.
8. (b) Aresta, M.; Quaranta, E. J. Org. Chem. 1988, 53, 4153.
9. (c) Aresta, M.; Quaranta, E. Ital. Pat. 1198206, 1988.
10. (d) Aresta, M.; Quaranta, E. J. Chem. Soc., Dalton Trans. 1992, 1893.
11. (e) Aresta, M.; Quaranta, E. Tetrahedron 1992, 48, 1515.
12. (f) Aresta, M.; Quaranta, E. Ital. Pat. 1237208, 1993.
13. 4. (a) Aresta, M.; Quaranta, E. Tetrahedron 1991, 47, 9489.
14. (b) Aresta, M.; Quaranta, E. Ital. Pat. 1237207, 1993.
15. 5. Aresta, M.; Berloco, C.; Quaranta, E. Tetrahedron 1995, 51, 8073.
16. 6. (a) Cahours, A. Ann. 1845, 56, 266.
17. (b) Bortnick, N.; Luskin, L. S.; Hurwitz, M.D.; Rytina, A.W. J. Am. Chem. Soc. 1956, 78, 4358.
18. (c) Hagemann, C. Kohlensaure derivate. In Methoden der Organischen Chemie; Houben-Weil, Eds.; G. Thieme Verlag: Stuttgart, 1983, 4th ed.; Band E4, p. 159.
19. 7. Adams, P.; Baron F.A. Chem. Rev. 1965, 65, 567.
20. 8. Massi Mauri, M.; Romano, U.; Rivetti, F. Ing. Chim. Ital. 1985, 21, 6 and references therein.
21. 9. Kock, P.; Romano, U. Ital. Pat. Appl. 20264 A/82.
22. 10. Romano, U.; Tesei, R. US Pat. 4045464, 1977.
23. 11. (a) Frulla, F.F.; Stuber, A.F.; Whitman, J.P. U.S. Pat. 4550188, 1985; Chem. Abstr. 1986, 104, 224725u.
24. (b) Giurgiolo, A.E. U.S. Pat. 4268684, 1981; Chem. Abstr. 1981, 96, 97407k.
25. (c) Giurgiolo, A.E. U.S. Pat. 4268683, 1981; Chem. Abstr. 1981, 95, 168832h.
26. (d) Romano, U.; Tesei, R. Ger. Offen. 2716540, 1977; Chem. Abstr. 1978, 88, 37459.
27. (e) Onoda, T.; Tano, K.; Hara, Y. Jap. Pat. Appl. 04316, 1980.
28. (f) Buysch, H.J.; Krimm, H.; Richter, W. Eur. Pat. Appl. 48371, 1982.
29. (g) Romano, U.; Fornasari, G.; Sgambato, U. Ital. Pat. Appl. 22967 A/82.
30. 12. (a) Anon., Res. Discl. 1987, 275, 162; Chem. Abstr. 1988, 108, 167429g.
31. 12. (a) Anon., Res. Discl. 1987, 275, 162; Chem. Abstr. 1988, 108, 167429g.
32. (b) Romano, U.; Fornasari, G.; Di Gioacchino, S. Ger. Offen. DE 3202690, 1982; Chem. Abstr. 1982, 97, 144607d.
33. (c) Mukai, T.; Suenobu, K.; Masago, M. Japan Kokai 77 14745, 1977; Chem. Abstr. 1977, 87, 52961e.
34. (c) Mukai, T.; Suenobu, K.; Masago, M. Japan Kokai 77 14745, 1977; Chem. Abstr. 1977, 87, 52961e.
35. 13. Yamazaki, N.; Higashi, F. Int. Prog. Urethanes 1980, 2, 61.
36. 14. (a) Knight W.B. Carboxyphosphate: Predicted Chemical Properties, Synthesis and Role as an Intermediate in Enzymic Reactions. In Enzymatic and Model Carboxylation and Reduction Reactions for Carbon Dioxide Utilization; Aresta, M.; Schloss, J.V. Eds.; Kluwer Academic Publishers: Dordrecht, 1990; NATO-ASI Series C, Vol. 314, p. 239.
37. (b) Rubio, V. Biochem. Soc. Trans. 1993, 21, 198.
38. 15. Aresta, M.; Bosetti, A.; Quaranta, E. Ital. Pat. Appl. 002202, 1996.
39. 16. Aresta, M.; Dibenedetto, A.; Quaranta, E. forthcoming paper
40. 17. A mixture of 1a (0.585 mmol) and DPC ( 12.2 mmol), heated at 363 K for 4 h in the absence of any catalyst, produced only traces of 3a, while 4a was obtained with a yield of 10 %.
41. 18. When 1b (0.655 mmol) was heated in DPC (11.2 mmol) at 363 K for 10 h, in the absence of any catalyst, only traces of 3b were obtained. 4b yield was not higher than 20 % (by HPLC).
42. 2P(O)OH (0.409 mmol) at 393 K for 72 hours.
43. 2P(O)OPh (0.083 mmol) heated at 363 K for 10 h afforded 3b and 4b with yield of 20 and 80 % (HPLC), respectively.
44. 2P(O)OPh was not found when a MeOH solution of the acid and DPC was stirred at 343 K for several hours. In this case, the GC-MS analysis of the reaction mixture revealed the formation of traces of PhOH and methylphenylcarbonate.
45. 22. Perrin, D.D.; Armarego, W.L.F.; Perrin, D.R. Purification of Laboratory Chemicals; Pergamon Press: Oxford, England, 1986.