Synthesis of diethyl α-(o-nitroaryl)phosphoglycines via oxidative nucleophilic substitution of hydrogen in nitroarenes

Synlett

Volumn , Issue 11, 2010, Pages 1666-1668

  Ma̧kosza, Mieczysaw ^a   Sulikowski, Daniel ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

amino acids; arylation; carbanions; oxidation

Indexed keywords

ALPHA (2 NITROARYL)PHOSPHOGLYCINE DERIVATIVE; AMMONIA; AROMATIC NITRO COMPOUND; HYDROGEN; NITRO DERIVATIVE; NITROBENZENE; PERMANGANATE POTASSIUM; PHOSPHORAMIDIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMER; NUCLEOPHILICITY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS;

EID: 77953881444     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219956     Document Type: Article

References (50)

1. Kafarski P, Lejczak B, Phosphorus, Sulfur Silicon Relat. Elem. 1991 63 193
2. De Lombaert S, Blanchard L, Stamfort L B., Tan J, Wallace E M., Satoh Y, Fitt J, Hoyer D, Simonsbergen D, Moliterni J, Marcopoulos N, Savage P, Chou M, Trapani A J., Jeng A Y., J. Med. Chem. 2000 43 488
3. Aminophosphonic and Aminophosphinic Acids Kukhar V P. Hudson H R. John Wiley and Sons Chichester 2000
4. Vassiliou S, Xeilari M, Yiotakis A, Germbecka J, Paweczak M, Kafarski P, Mucha A, Bioorg. Med. Chem. Lett. 2007 15 3187
5. Hirschmann R, Smith A B. III., Taylor C M., Benkovic P A., Taylor S D., Yager K M., Sprengler P A., Benkovic S J., Science 1994 265 234
6. Smith A B. III., Taylor C M., Bencovic S J., Hirschmann R, Tetrahedron Lett. 1994 35 6853
7. Grembecka J, Mucha A, Cierpicki T, Kafarski P, [nl]J. Med. Chem. 2003 46 2641
8. Moore J D., Sprott K T., Hanson P R., J. Org. Chem. 2002 67 8123
9. Liu W, Rogers C J., Fisher A J., Toney M D., Biochemistry 2002 41 12320
10. Osipov S N., Artyushin O I., Kolomiets A F., Bruneau C, Dixneuf P H., Synlett 2000 1031
11. Ranu B C., Hajra A, Jana U, Org. Lett. 1999 1 1141
12. Huang J, Chen R, Heteroat. Chem. 2000 11 480
13. Maier L, Diel P J., Phosphorous, Sulfur Silicon Relat. Elem. 1994 90 259
14. Yager K M., Taylor C M., Smith A B. III., J. Am. Chem. Soc. 1994 116 9377
15. Lavielle G, Hautefaye P, Schaeffer C, Boutin J A., Cudennec C A., Pierre A, J. Med. Chem. 1991 34 1998
16. Schmidt U, Krause H W., Oehme G, Michalik M, Fischer K, Chirality 1998 10 564
17. Ordonez M, Rojas-Cabrera H, Cativiela C, Tetrahedron 2009 65 17
18. Kabachnik M J., Medvev T Y., Dokl. Akad. Nauk SSSR 1952 83 689
19. Fields E K., J. Am. Chem. Soc. 1952 74 1528
20. Lee S.-G, Lee J K., Song C E., Kim D.-C, Bull. Korean Chem. Soc. 2002 667
21. Matveeva E D., Podrugina T A., Tishkovskaja E V., Tomilova L G., Zefirov N S., Synlett 2003 2311
22. Joly G D., Jacobsen E N., J. Am. Chem. Soc. 2004 126 4102
23. Wu J, Sun W, Xia H.-G, Sun X, Org. Biomol. Chem. 2006 4 1663
24. Bhagat S, Chakraborti A K., J. Org. Chem. 2007 72 1263
25. Mikoajczyk M, ywa P, Drabowicz J, Tetrahedron: Asymmetry 1997 8 3991
26. Mikoajczyk M, ywa P, Drabowicz J, Tetrahedron: Asymmetry 2002 13 2571
27. Mikoajczyk M, J. Organomet. Chem. 2005 690 2488
28. Kolesnichenko G A., Malykhin E V., Shteingarts V D., Zh. Org. Khim. 1986 22 806
29. Counotte-Potman A, vanderPlas H C., J. Heterocycl. Chem. 1981 18 123
30. VanderPlas H C., Woniak M, Croat. Chim. Acta 1986 59 33
31. Woniak M, vanderPlas H C., Acta Chem. Scand. 1993 47 95
32. Stern K M., Cheng B K., Hilman F D., Allman J M., J. Org. Chem. 1994 59 5627
33. Ma̧kosza M, Paszewski M, Sulikowski D, Synlett 2008 2938
34. Ma̧kosza M, Surowiec M, Szczepaska A, Sulikowski D, Maltsev O, Synlett 2007 470
35. Ma̧kosza M, Sulikowski D, Maltsev O, Synlett 2008 1711
36. Ma̧kosza M, Staliski K, Chem. Eur. J. 1997 3 2025
37. Ma̧kosza M, Staliski K, Synthesis 1998 1631
38. Ma̧kosza M, Staliski K, Tetrahedron 1998 54 8797
39. Ma̧kosza M, Staliski K, Pol. J. Chem. 1999 73 151
40. Ma̧kosza M, Kamieska-Trela K, Paszewski M, Bechcicka M, Tetrahedron 2005 61 11952
41. Bartoli G, Acc. Chem. Res. 1984 17 109
42. Ma̧kosza M, Sypniewski M, Tetrahedron 1994 50 4913
43. Ma̧kosza M, Paszewski M, Synthesis 2002 2203
44. Ma̧kosza M, Sulikowski D, J. Org. Chem. 2009 74 3827
45. Bartoli G, Bosco M, Melandri A, Boicelli C, J. Org. Chem. 1979 44 2087
46. Oberhauser T, Meduna V, Tetrahedron 1996 52 7691
47. Hoppe D, Beckmann L, Liebigs Ann. Chem. 1979 2066
48. Appel R, Loos H, Mayr H, J. Am. Chem. Soc. 2009 131 704
49. Ma̧kosza M, Glinka T, Kinowski A, Tetrahedron 1984 40 1863
50. Ma̧kosza M, Wenall M, Goliski J, Kinowski A, Bull. Pol. Acad. Chem. 1985 33 427