Mild and convenient N-formylation protocol in water-containing solvents

Tetrahedron Letters

Volumn 54, Issue 16, 2013, Pages 2077-2081

  Aleiwi, Bilal A ^a   Mitachi, Katsuhiko ^a   Kurosu, Michio ^a  

^a UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

Author keywords

Amino acids; Daptomycin; Glyceroacetonide Oxyma; Kanamycin; N formylation; Reactions in water media; Spectinomycin; Water soluble Oxyma

Indexed keywords

(2,2 DIMETHYL 1,3 DIOXOLAN 4 YL)METHYL 2 CYANO 2 (HYDROXYIMINO)ACETATE; ALPHA AMINO ACID; AMINE; CARBOXYLIC ACID; DAPTOMYCIN; PHENYLALANINE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; COUPLING FACTOR; DRUG SCREENING; FORMYLATION; POLYMERIZATION; TEMPERATURE;

EID: 84875216536     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.02.013     Document Type: Article

References (59)

1. F.F. Blicke, and C.-J. Lu J. Am. Chem. Soc. 74 1952 3933
2. J.C. Sheehan, and D.-D.H. Yang J. Am. Chem. Soc. 80 1958 1154
3. G.R. Pettit, and E.G. Thomas J. Org. Chem. 24 1959 895
4. H.A. Staab, and B. Polenski Liebigs Ann. Chem. 655 1962 95
5. H.L. Yale J. Org. Chem. 36 1971 3238
6. M.A. Kraus Synthesis 1973 361
7. F. Effenberger, A.O. Muck, and E. Bessey Chem. Ber. 113 1980 2086
8. M. Waki, and J. Meienhofer J. Org. Chem. 42 1977 2019
9. F. Effenberger, and E. Bessey Chem. Ber. 113 1980 2100
10. F. Effenberger, M. Keil, and E. Bessey Chem. Ber. 113 1980 2110
11. J.C. Gramain, and R. Rémuson Synthesis 1982 264
12. J. Martinez, and J. Laur Synthesis 1982 979
13. H. Yazawa, and S. Goto Tetrahedron Lett. 26 1985 3703
14. L. Kisfaludi, and L. Ötvös Jr. Synthesis 1987 510
15. G.A. Olah, L. Ohannesian, and M. Arvanaghi Chem. Rev. 87 1987 671
16. P. Strazzolini, A.G. Giumanini, and S. Cauci Tetrahedron 46 1990 1081
17. M. Neveux, C. Bruneau, and P.H. Dixneuf J. Chem. Soc., Perkin Trans. 1 1991 1197
18. A.R. Katritzky, H.-X. Chang, and B. Yang Synthesis 1995 503
19. W. Duczek, J. Deutsch, S. Vieth, and H.-J. Niclas Synthesis 1996 37
20. M.B. Berry, J. Blagg, D. Craig, and M.C. Willis Synlett 1992 659
21. N. Akikusa, K. Mitsui, T. Sakamoto, and Y. Kikugawa Synthesis 1992 1058
22. T. Chancellor, and C. Morton Synthesis 1994 1023
23. T. Giard, D. Be'nard, and J.C. Plaquevent Synthesis 1998 297
24. T. Meinnel, L. Patiny, S. Ragusa, and S. Blanquet Biochemistry 38 1999 4287
25. P.G. Reddy, G.D.K. Kumar, and S. Baskaran Tetrahedron Lett. 41 2000 9149
26. D.R. Hill, C.-N. Hsiao, R. Kurukulasuriya, and S.J. Wittenberger Org. Lett. 4 2002 111
27. T. Cochet, V. Bellosta, A. Greiner, D. Roche, and J. Cossy Synlett 2011 1920 see Ref. 2
28. S.H. Jung, J.H. Ahn, S.K. Park, and J.-K. Choi Bull. Korean Chem. Soc. 23 2002 149
29. M. Mihara, Y. Ishino, S. Minakata, and M. Komatsu Synthesis 2003 2317
30. L. De Luca, G. Giacomelli, A. Porcheddu, and M. Salaris Synlett 2004 2570
31. N. Iranpoor, H. Firouzabadi, and A. Jamalian Tetrahedron Lett. 46 2005 7963
32. A.K. Bose, S.N. Ganguly, M.G. Manhas, A. Guha, and E. Pombo-Villars Tetrahedron Lett. 47 2006 4605
33. M. Hosseini-Sarvari, and H. Shargi J. Org. Chem. 71 2006 6652
34. B. Das, M. Krishnaiah, P. Balasubramanyam, B. Veeranjaneyulu, and D.N. Kumar Tetrahedron Lett. 49 2008 2225
35. A. Chandra Shekhar, A. Ravi Kumar, G. Sathaiah, V. Luke Paul, M. Sridhar, and P. Shanthan Rao Tetrahedron Lett. 50 2009 7099
36. O. Saidi, M.J. Bamford, A.J. Blacker, J. Lynch, S.P. Marsden, P. Plucinski, R.J. Watson, and J.M.J. Willimas Tetrahedron Lett. 51 2010 5804
37. J.-G. Kim, and D.O. Jang Synlett 2010 1231
38. F.M.F. Chen, and N.L. Benoiton Synthesis 1979 709
39. G. Brahmachari, and S. Laskar Tetrahedron Lett. 51 2010 2319
40. M. Lei, L. Ma, and L. Hu Tetrahedron Lett. 51 2010 4186
41. L.A. Shastri, S.L. Shastri, C.D. Bathula, M. Basanagouda, and M.V. Kulkarni Synth. Commun. 41 2011 476
42. B. Krishnakumar, and M. Swaminathan J. Mol. Catal. A: Chem. 334 2011 98
43. M. SuchÝ, A.A.H. Elmehriki, and R.H.E. Hudson Org. Lett. 13 2011 3952
44. Y. Wang, B.A. Aleiwi, Q. Wang, and M. Kurosu Org. Lett. 14 2012 4910
45. Q. Wang, Y. Wang, and M. Kurosu Org. Lett. 14 2012 3372
46. S.N. Khattab Bull. Chem. Soc. Jpn. 83 2010 1374
47. A. El-Faham, R. Subiros-Funosas, and F. Albericio Chem. Eur. J. 19 2010 3641
48. R. Subiros-Funosas, R. Prohens, R. Barbas, A. El-Faham, and F. Albericio Chem. Eur. J. 15 2009 9394
49. 3 solution.
50. 2 and COOH or OH groups.
51. Difference in reactivity of the nitrogen atoms in kanamycin and amikacin, see: S. Hanessian, A. Kornienkoa, and E.E. Swayze Tetrahedron 59 2003 995
52. S. Bera, G.G. Zhanel, and F. Schweizer J. Med. Chem. 53 2010 3626
53. H. Kawaguchi, T. Naito, S. Nakagawa, and K. Fujisawa Antibiotics 25 1972 695
54. M.P. Mingeot-Leclercq, Y. Glupczynski, and P.M. Tulkens Antimicrob. Agents Chemother. 43 1999 727
55. M.P. Mingeot-Leclercq, and P.M. Tulkens Antimicrob. Agents Chemother. 43 1999 1003
56. B. Andre Antimicrob. Agents Chemother. 2005 470
57. M. Peeters Antimicrob. Agents Chemother. 26 1984 608
58. M. Sanson-Lepors Antimicrob. Agents Chemother. 30 1986 512
59. M. Debono, M. Barnhart, C.B. Carrell, J.A. Hoffmann, J.L. Occolowitz, B.J. Abbott, D.S. Fukuda, R.L. Hamill, K. Biemann, and W.C. Herlihy J. Antibiot. 40 1987 761