Synthesis of N-urethane protected α-aminoalkyl-α-cyanomethyl ketones; Application to the synthesis of 3-substituted 5-amino-1H-pyrazole tethered peptidomimetics

Synlett

Volumn 23, Issue 13, 2012, Pages 1913-1918

  Sharnabai, M K ^a   Nagendra, G ^a   Sureshbabu, Vommina V ^a  

^a BANGALORE UNIVERSITY   (India)

Author keywords

amino acid mimics; ketones; peptidomimetics; pyrazole

Indexed keywords

ALPHA AMINOALKYL ALPHA CYANOMETHYL KETONE DERIVATIVE; KETONE DERIVATIVE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG; URETHAN;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; RACEMIZATION; SYNTHESIS;

EID: 84864049906     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1316586     Document Type: Article

References (32)

1. Rijkers DT. S, Van Esse GW, Merkx R, Brouwer AJ, Jacobs HJ. F, Pieters RJ, Liskamp RM. J. Chem. Commun.: 2005; 4581
2. Sureshbabu VV, Shankar AN, Hemantha HP, Narendra N, Ushati D, Guru Row TN. J. Org. Chem.: 2009; 74 5260
3. Ugi I. Isonitrile Chemistry. Academic Press New York/London: 1971
4. Zhu J, Wu X, Danishefsky SJ. Tetrahedron Lett.: 2009; 50 577
5. Sureshbabu VV, Narendra N, Nagendra G. J. Org. Chem.: 2009; 74 153
6. Sureshbabu VV, Venkataramanarao R, Shankar AN, Chennakrishnareddy G. Tetrahedron Lett.: 2007; 48 7038
7. Demko ZP, Sharpless KB. Org. Lett.: 2002; 4 2525
8. Angell YL, Burgess K. Chem. Soc. Rev.: 2007; 36 1674
9. Huisgen R. 1,3-Dipolar Cycloaddition-Introduction, Survey, Mechanism In 1,3-Dipolar Cycloaddition Chemistry. Padwa A. Wiley New York: 1984; 1 176
10. Falorni M, Giacomelli G, Spanu E. Tetrahedron Lett.: 1998; 39 9241
11. Domling A, Ugi I. Angew. Chem. Int. Ed.: 2000; 39 3169
12. Domling A. Chem. Rev.: 2006; 106 17
13. Maareseveen JH. V, Horne WS, Ghadiri MR. Org. Lett.: 2005; 7 4503
14. Pedersen DS, Abell A. Eur. J. Org. Chem.: 2011; 2399
15. Abell AD. Lett. Pept. Sci.: 2002; 8 267
16. Spatola AF. In Chemistry and Biochemistry of Amino Acids, Peptides and Proteins. Vol. 7 Weinstein B. Dekker New York: 1983; 267
17. Reeder MR, Anderson RM. Chem. Rev.: 2006; 106 2828
18. Birch PL, El-Obeid HA, Akthar M. Arch. Biochem. Biophys.: 1972; 148 447
19. Albek A, Persky R. Tetrahedron: 1994; 50 6333
20. Beaulieu PL, Wernic D, Duceppe J.-S, Guindon Y. Tetrahedron Lett.: 1995; 36 3317
21. Onishi T, Hirose N, Nakano T, Nakazawa M, Izawa K. Tetrahedron Lett.: 2001; 42 5883
22. Izawa K, Onishi T. Chem. Rev.: 2006; 106 2811
23. Beaulieu PL, Lavallee A, Abraham A, Anderson PC, Boucher C, Bousquet Y, Duceppe J.-S, Gillard J, Gorys V, Grand-Maitre C, Grenier L, Guindon Y, Guse I, Plamondon L, Soucy F, Valois S, Wernic D, Yoakim C. J. Org. Chem.: 1997; 62 3440
24. Goodman M, Felix A, Moroder L, Toniolo C. Houben - Weyl: Synthesis of Peptides & Peptidomimetics. Vol. E22c Georg Thieme Verlag Stuttgart: 2003; 393 395
25. Narendra N, Vishwanatha TM, Sureshbabu VV. Int. J. Pept. Res. Ther.: 2010; 16 283
26. Rotella DP. Tetrahedron Lett.: 1995; 36 5453
27. Bazewicz CG, Lipkin JS, Lozinak KA, Watson MD, Brewer SH. Tetrahedron Lett.: 2011; 52 6865
28. Rappaport Z. The Chemistry of the Cyano Group. Interscience Publishers London, England: 1970
29. Jones G. Org. React.: 1967; 15 204
30. Robichaud BA, Liu KG. Tetrahedron Lett.: 2011; 52 6935
31. Brillon D, Sauve G. J. Org. Chem.: 1992; 57 1838
32. Sauve G, Le Berre N, Zacharie B. J. Org. Chem.: 1990; 55 3002