Mild and efficient synthesis of carbazates and dithiocarbazates via a three-component coupling using Cs2CO3 and TBAI

Tetrahedron Letters

Volumn 45, Issue 2, 2004, Pages 401-405

  Fox, Daniel L ^a   Ruxer, John T ^a   Oliver, John M ^a   Alford, Kasey L ^a   Salvatore, Ralph Nicholas ^a  

^a WESTERN KENTUCKY UNIVERSITY   (United States)

Author keywords

Azadepsipeptide; Carbazates; Cesium carbonate; Dithiocarbazates; Hydrazine

Indexed keywords

ALKYL GROUP; CARBON DIOXIDE; CARBONIC ACID DERIVATIVE; CESIUM; CESIUM CARBONATE; HYDRAZINE; HYDRAZINE DERIVATIVE; PEPTIDE DERIVATIVE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; REACTION ANALYSIS; ROOM TEMPERATURE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0345735501     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.144     Document Type: Article

References (55)

1. (a) Hydrazine and its Derivatives. 4th ed. Kirk-Othmer Encyclopedia of Chemical Technology. Vol. 13:1995;Wiley, New York
2. (b) Schmidt E.W. Hydrazine and its Derivatives Preparation, Properties, Applications. 2nd ed. 2001;Wiley-Interscience, New York
3. (c) Ragnarsson U. Chem. Soc. Rev. 30:2001;205-213
4. (d) Atkinson R.S. Barton D., Ollis W.D. Comprehensive Organic Synthesis. Vol. 2:1979;219 Pergamon, London
5. (e) Patai S. Chemistry of Hydrazo-, Azo- and Azoxy Groups. 1975;Wiley, New York. Chapter 4.
6. (a) Sakakibara S., Honda I., Naruse M., Kanaoka M. Experientia. 25:1969;576
7. (b) Makarova E.A., Kosheleva G.N. Metody Polucheniya Khim. Reakt. I Preparatov. 17:1967;26-28
8. (c) Sakakisbara S., Honda I., Takada K., Miyoshi M., Ohnishi T., Okumura K. Bull. Chem. Soc. Jpn. 42:1969;809
9. (d) Ito M., Morino D. Experientia. 24:1968;101
10. (e) Honda I., Shimonishi Y., Sakakibara S. Bull. Chem. Soc. Jpn. 40:1967;2415
11. (f) Quibell M., Turnell W.G., Johnson T. J. Chem. Soc., Perkin Trans. 1. 22:1993;2843
12. (g) Sofuku S., Mizumura M., Hagitani A. Nippon Kagaku Zasshi. 89:1968;721
13. h) Gray C.J., Quibell M., Baggett N., Hammerle T. Int. J. Pept. Protein Res. 40:1992;351.
14. (a) Connolly T.J., Crittall A.J., Ebrahim A.S., Ji G. Org. Process Res. Dev. 4:2000;526
15. (b) Henriksen L., Jensen O.R. Acta Chem. Scand. 22:1968;3042
16. (c) Dovlatyan V.V., Avetissyan F.V., Papoyan T.Z., Gevorgyan R.A., Kinoyan F.S. Khim. Zh. Aremenii. 54:2001;85
17. (d) Nesynov E.P., Pel'kis P.S. Zh. Prganicheskoi Khimii. 4:1968;837
18. (e) Delaby R., Brustlein F., Warolin C., Chabrier P. Bull. Soc. Chim. Fr. 1961;2056
19. (f) Eloy F., Moussebois C. Bull. Soc. Chim. Belges. 68:1959;423
20. (g) Eloy F., Moussebois C. Bull. Soc. Chim. Belges. 68:1959;409
21. (h) Hauser M. J. Org. Chem. 31:1966;968
22. (i) Hanefeld W., Schlitzer M. Arch Pharm. 327:1994;413
23. (j) Lalezari I. J. Heterocycl. Chem. 22:1985;741
24. (k) Gordon M.S., Krause J.G., Linneman-Mohr M.A., Parchue R.R. Synthesis. 3:1980;244
25. (l) Zinner G., Krause T., Doerschner K. Arch Pharm. 310:1977;642
26. (m) Clive D.L.J., Denyer C.V. J. Chem. Soc., Chem. Commun. 18:1971;1112.
27. (a) Dutta S.K., Samanta S., Ghosh D., Butcher R.J., Chaudhury M. Inorg. Chem. 41:2002;5555
28. (b) Bellerby J.M., Edwards D.A., Thompsett D. Inorg. Chim. Acta. 117:1986;L31
29. (c) dos Santo-Filho F., Kaiser P., Roland C., Momesso M.A. J. Brazilian Chem. Soc. 5:1994;97
30. (d) Huan D., Zhiming G., Zhijian H. Wuji Huaxue Xuebao. 5:1989;73
31. (e) Karra R., Singh Y.P., Rai A.K. Phosphorus, Sulfur, Silicon Relat. Elem. 166:2000;125
32. (f) Chauhan A.K.S., Misra M. J. Indian Chem. Soc. 70:1993;148.
33. (a) Marchand-Brynaert J. Farmaco. 50:1995;455
34. (b) Dorn C.P., Zimmermann M., Yang S.S., Yurewicz E.C., Ashe B.M., Frankshun R., Jones H. J. Med. Chem. 20:1977;1464
35. (c) Dorn, C. P.; Yang, S. S. U.S. Patent P2658254.7, 1975
36. (d) Shemyakin M.M., Ovchinnikov Yu.A., Kiryushkin A.A., Ivanov V.T. Tetrahedron Lett. 1963;885.
37. Nagle A.S., Salvatore R.N., Cross R.M., Kapxhiu E.A., Sahab S., Yoon C.H., Jung K.W. Tetrahedron Lett. 44:2003;5695.
38. Dyker H., Scherkenbeck J., Gondol D., Goehrt A., Harder A. J. Org. Chem. 66:2001;3760.
39. (a) Dutta A.S., Morley J.S. J. Chem. Soc., Perkin Trans. 1. 1975;1712
40. (b) Nara S., Sakamoto T., Miyazawa E., Kikugawa Y. Synth. Commun. 33:2003;87. and references cited therein
41. (c) Biel J.H., Drukker A.E., Mitchell T.F., Sprengeler E.P., Nuhfer P.A., Conway A.C., Horita A. J. Am. Chem. Soc. 81:1959;2805.
42. 2) incorporation and/or stabilizing the incipient anion through the conjugation with the tetrabutylammonium cation. In the absence of TBAI, poor product yields resulted along with side products stemming from direct N-alkylation. For similar results using TBAI in faciliating carbamate and carbonate formation, see: Salvatore R.N., Chu F., Nagle A.S., Kapxhiou E.A., Cross R.M., Jung K.W. Tetrahedron. 58:2002;3329. Also, tetrabutylammonium bromide (TBAB) and various other onium salts have been utilized in supercritical carbon dioxide for the selective formation of urethanes. See: Yoshida M., Hara N., Okuyama S. Chem. Commun. 2000;151.
43. 2) incorporation and/or stabilizing the incipient anion through the conjugation with the tetrabutylammonium cation. In the absence of TBAI, poor product yields resulted along with side products stemming from direct N-alkylation. For similar results using TBAI in faciliating carbamate and carbonate formation, see: Salvatore R.N., Chu F., Nagle A.S., Kapxhiou E.A., Cross R.M., Jung K.W. Tetrahedron. 58:2002;3329. Also, tetrabutylammonium bromide (TBAB) and various other onium salts have been utilized in supercritical carbon dioxide for the selective formation of urethanes. See: Yoshida M., Hara N., Okuyama S. Chem. Commun. 2000;151.
44. (a) For other chemoselective N-alkylations using cesium bases, see: Salvatore R.N., Shin S.I., Nagle A.S., Jung K.W. J. Org. Chem. 66:2001;1035
45. (b) Salvatore R.N., Flanders V.L., Ha D., Jung K.W. Org. Lett. 2:2000;2797
46. (c) Butcher K.J. Synlett. 1994;825
47. (d) McGhee W., Riley D., Christ K., Pan Y., Parnas B. J. Org. Chem. 60:1995;2820
48. (e) Salvatore R.N., Nagle A.S., Jung K.W. J. Org. Chem. 67:2002;674
49. (f) Salvatore R.N., Schmidt S.E., Shin S.I., Nagle A.S., Worrell J.H., Jung K.W. Tetrahedron Lett. 41:2000;9705
50. (g) Salvatore R.N., Ledger J.A., Jung K.W. Tetrahedron Lett. 42:2001;6023
51. (h) Salvatore R.N., Nagle A.S., Schmidt S.E., Jung K.W. Org. Lett. 1:1999;1893.
52. 2: C, 67.17; H, 8.86; N, 11.19. Found: C, 67.12; H, 8.82; N, 11.21.
53. 2: C, 53.30; H, 6.71; N, 10.36. Found: C, 53.26; H, 6.65; N, 10.33.
54. Nagle A.S., Salvatore R.N., Chong B.D., Jung K.W. Tetrahedron Lett. 41:2000;3011.
55. 13C NMR, and 2D NMR analysis indicate the product as a single diastereomer.