α-amidoalkylating agents from N-acyl-α-amino acids: 1-(N-acylamino)alkyltriphenylphosphonium salts

Journal of Organic Chemistry

Volumn 77, Issue 4, 2012, Pages 1952-1960

  Mazurkiewicz, Roman ^a   Adamek, Jakub ^a   Październiok Holewa, Agnieszka ^a   Zielińska, Katarzyna ^a   Simka, Wojciech ^a   Gajos, Anna ^a   Szymura, Karol ^a  

^a SILESIAN UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EQUIMOLAR AMOUNT; METHOXY GROUP; METHOXYLATION; PROTEINOGENIC; ROOM TEMPERATURE; SIDE-CHAINS; TETRAFLUOROBORATES; TWO-STEP PROCEDURE;

AMIDES; ELECTROCHEMICAL OXIDATION; PRECIPITATION (CHEMICAL); SALTS; SILICA GEL; SILICON COMPOUNDS;

AMINO ACIDS;

1 (N ACYLAMINO)TRIPHENYLPHOSPHONIUM DERIVATIVE; ALKYLATING AGENT; ALPHA AMIDOALKYLATING AGENT; AMIDE; AMINO ACID DERIVATIVE; CYSTEINE; METHIONINE; N ACYL ALPHA AMINO ACID DERIVATIVE; PHOSPHONIUM DERIVATIVE; PIPERIDINE; SILICON DIOXIDE; TRIPHENYLPHOSPHONIUM TETRAFLUOROBORATE; TRYPTOPHAN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTROCHEMISTRY; ELECTROLYSIS; HOFER MOEST REACTION; PRECIPITATION; REACTION ANALYSIS; REPRODUCIBILITY; STOICHIOMETRY; SYNTHESIS;

ACYLATION; ALKYLATING AGENTS; AMIDES; AMINO ACIDS; BORIC ACIDS; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOPHOSPHORUS COMPOUNDS; OXIDATION-REDUCTION; SILICON DIOXIDE;

EID: 84857205653     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202534u     Document Type: Article

References (47)

1. Zaug, H. E. Synthesis 1970, 49-73
2. Zaug, H. E. Synthesis 1984, 85-110
3. Zaug, H. E. Synthesis 1984, 181-212
4. Katrizky, A. R.; Manju, K.; Singh, S. K.; Meher, N. K. Tetrahedron 2005, 61, 2555-2581
5. Katrizky, A. R.; Lan, X.; Yang, J. Z.; Denisko, O. V. Chem. Rev. 1998, 98, 409-548
6. Petrini, M. Chem. Rev. 2005, 105, 3949-3977
7. Zoller, U.; Ben-Ishai, D. Tetrahedron 1975, 31, 863-866
8. Caputo, R.; Cassano, E.; Longobardo, L.; Palumbo, G. Tetrahedron 1995, 51, 12337-12350
9. Caputo, R.; Cassano, E.; Longobardo, L.; Palumbo, G. Tetrahedron Lett. 1995, 36, 167-168
10. Marianacci, O.; Micheletti, G.; Bernardi, L.; Fini, F.; Fochi, M.; Pettersen, D.; Sgarzani, V.; Ricci, A. Chem.-Eur. J. 2007, 13, 8338-8351
11. Das, B.; Damodar, K.; Bhunia, N. J. Org. Chem. 2009, 74, 5607-5609
12. Katrizky, A. R.; Pernak, J.; Fan, W.-Q.; Saczewski, F. J. Org. Chem. 1991, 56, 4439-4443
13. Katrizky, A. R.; Fan, W.-Q.; Black, M.; Pernak, J. J. Org. Chem. 1992, 57, 547-549
14. Katrizky, A. R.; Lan, X.; Yang, J. Z.; Fan, W.-Q. Synthesis 1994, 445-456
15. Mazurkiewicz, R.; Październiok-Holewa, A.; Grymel, M. Tetrahedron Lett. 2008, 49, 1801-1803
16. Mazurkiewicz, R.; Październiok-Holewa, A.; Grymel, M. Phosphorus, Sulfur Silicon Relat. Elem. 2009, 184, 1017-1027
17. Mazurkiewicz, R.; Październiok-Holewa, A.; Orlińska, B.; Stecko, S. Tetrahedron Lett. 2009, 50, 4606-4609
18. Mazurkiewicz, R.; Pierwocha, A. Monatsh. Chem. 1996, 127, 219-225
19. Mazurkiewicz, R.; Pierwocha, A. Monatsh. Chem. 1997, 128, 893-900
20. Mazurkiewicz, R.; Październiok-Holewa, A.; Kononienko, A. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 1986-1992
21. Mazurkiewicz, R.; Adamek, J.; Mrowiec-Białoń, J.; Październiok-Holewa, A. Thermochim. Acta 2011, 512, 22-27
22. Mazurkiewicz, R.; Październiok-Holewa, A.; Adamek, J.; Zielińska, K.; Piernikarczyk, K. Arkivoc, in press.
23. Linstead, R. P.; Shephard, B. R.; Weedon, B. C. L. J. Chem. Soc. 1951, 2854-2858
24. Horikawa, H.; Iwasaki, T.; Matsumoto, K.; Miyoshi, M. Tetrahedron Lett. 1976, 17, 191-194
25. Iwasaki, T.; Horikawa, H.; Matsumoto, K.; Miyoshi, M. J. Org. Chem. 1977, 42, 2419-2423
26. Iwasaki, T.; Horikawa, H.; Matsumoto, K.; Miyoshi, M. J. Org. Chem. 1979, 44, 1552-1554
27. Iwasaki, T.; Horikawa, H.; Matsumoto, K. Bull. Soc. Chem. Jpn 1979, 52, 826-830
28. Lund, H.; Hammerlich, O. Organic Electrochemistry; Marcel Dekker: New York, 2001.
29. Tajima, T.; Kurihara, H.; Fuchigami, T. J. Am. Chem. Soc. 2007, 129, 6680-6681
30. Matsumura, Y.; Tanaka, T.; Wanyoike, G. N.; Maki, T.; Onomura, O. J. Electroanal. Chem. 2001, 507, 71-74
31. Matsumura, Y.; Wanyoike, G. N.; Onomura, O.; Maki, T. Electrochim. Acta 2003, 48, 2957-2966
32. Wanyoike, G. N.; Onomura, O.; Maki, T.; Matsumura, Y. Org. Lett. 2002, 11, 1875-1877
33. Onomura, O. Yakugaku Zasshi 2002, 122, 983-987
34. Zietlow, A.; Steckhan, E. J. Org. Chem. 1994, 59, 5658-5661
35. Kardasis, G.; Brungs, P.; Steckhan, E. Tetrahedron 1998, 54, 3471-3478
36. Seebach, D.; Charczuk, R.; Gerber, Ch.; Renaud, P. Helv. Chim. Acta 1989, 72, 401-425
37. Matsumura, Y.; Shirakawa, Y.; Satoh, Y.; Umino, M.; Tanaka, T.; Maki, T.; Onomura, O. Org. Lett. 2000, 2, 1689-1691
38. Wieber, G. M.; Hegedus, L. S.; Akermark, B.; Michalson, E. T. J. Org. Chem. 1989, 54, 4649-4653
39. Oftring, A.; Hahn, E.; Fikentscher, R. German Patent 3,520,829, 1986.
40. WSS: Spectral data were obtained from Wiley Subscription Services, Inc. (U.S.).
41. Matsuo, J.; Tanaki, Y.; Kido, A.; Ishibashi, H. Chem. Commun. 2006, 2896-2898
42. Chorev, M.; MacDonald, S. A.; Goodman, M. J. Org. Chem. 1984, 49, 821-827
43. Phan, X. T.; Shannon, P. J. J. Org. Chem. 1983, 48, 5164-5170
44. Krebs, A.; Bolm, C. Tetrahedron 2011, 67, 4055-4060
45. Harding, E. K.; Liu, L. T.; Farrar, D. G.; Coleman, M. T.; Tansey, S. K. Synth. Commun. 1991, 21, 1409-1417
46. Kise, N.; Ueda, N. J. Org. Chem. 1999, 64, 7511-7514
47. Shono, T.; Matsumura, Y.; Uchida, K.; Tsubata, K.; Makino, A. J. Org. Chem. 1984, 49, 300-304