Efficient synthesis of new 4-arylideneimidazolin-5-ones related to the GFP chromophore by 2+3 cyclocondensation of arylideneimines with imidate ylides

Synthesis

Volumn , Issue 14, 2010, Pages 2424-2436

  Baldridge, Anthony ^a   Kowalik, Janusz ^a   Tolbert, Laren M ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

2+3 cycloaddition; 4 arylideneimidazolin 5 one; azomethine ylide; heterocycle; Schiff bases

Indexed keywords

AROMATIC ALDEHYDE; AZOMETHINE YLIDES; CYCLOCONDENSATION; EFFICIENT SYNTHESIS; GREEN FLUORESCENT PROTEIN; HETEROCYCLE; HETEROCYCLES; PRIMARY AMINES; SCHIFF BASIS;

ALDEHYDES; CHROMOPHORES; FUNCTIONAL GROUPS;

ORGANIC POLYMERS;

4 ARYLIDENEIMIDAZOLIN 5 ONE DERIVATIVE; ARYLIDENEIMINE DERIVATIVE; GREEN FLUORESCENT PROTEIN; IMIDATE YLIDE DERIVATIVE; IMIDAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOPHORE; COLUMN CHROMATOGRAPHY; CYCLOADDITION; DENATURATION; HYDROPHOBICITY; METHODOLOGY; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 77954599570     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218796     Document Type: Article

References (42)

1. Tonge P J., Meech S R., J. Photochem. Photobiol., A 2009 205 1
2. Wu L, Burgess K, J. Am. Chem. Soc. 2008 130 4089
3. Chen K.-Yu, Cheng Y.-M, Lai C.-H, Hsu C.-C, Ho M.-L, Lee G.-H, Chou P.-T, J. Am. Chem. Soc. 2007 129 4534
4. Baldridge A, Samanta S R., Jayaraj N, Ramamurthy V, Tolbert L M., J. Am. Chem. Soc. 2010 132 1498
5. Even though Emil Erlenmeyer is customarily credited with this discovery (see ref. 5a), an earlier report on the reaction of hippuric acid with benzaldehyde and acetic anhydride actually came from J. Plöchl (see ref. 5b).
6. Erlenmeyer E, Justus Liebigs Ann. Chem. 1893 275 1
7. Plöchl J, Ber. Dtsch. Chem. Ges. 1883 16 2815
8. Erlenmeyer E, Ber. Dtsch. Chem. Ges. 1900 33 2036
9. Kropp W, Decker H, Ber. Dtsch. Chem. Ges. 1909 42 1184
10. Williams D L., Ronzio A R., J. Am. Chem. Soc. 1946 68 647
11. Islam A M., Khalil A M., AbdEl-Gawad I I., Aust. J. Chem. 1973 26 827
12. Badr M Z., El-Sherief H A. H., Tadros M E., Bull. Chem. Soc. Jpn. 1982 55 2267
13. Islam A M., Khalil A M., El-Houseni M S., Aust. J. Chem. 1973 26 1701
14. He X, Bell A F., Tonge P J., Org. Lett. 2002 4 1523
15. Chen K.-Y, Cheng Y.-M, Lai C.-H, Hsu C.-C, Ho M.-L, Lee G.-H, Chou P.-T, J. Am. Chem. Soc. 2007 129 4534
16. Kojima S, Okhawa H, Hirano T, Maki S, Niwa H, Ohashi M, Inouye S, Tsui F I., Tetrahedron Lett. 1998 5239
17. Kawasaki A, Maekawa K, Kubo K, Igarashi T, Sakurai T, Tetrahedron 2004 60 9517
18. Wu L, Burgess K, J. Am. Chem. Soc. 2008 130 4089
19. Lerestif J M., Bazureau J P., Hamelin J, Tetrahedron Lett. 1993 4639
20. Devasia G, Tetrahedron Lett. 1976 571
21. Niwa H, Inouye S, Hirano T, Matsuno T, Kojima S, Kubota M, Ohashi M, Tsui F I., Proc. Natl. Acad. Sci. U.S.A. 1996 93 13617
22. Oumouch S, Bourotte M, Schmitt M, Bourguignon J.-J, Synthesis 2005 25
23. Bhattacharjya G, Agasti S S., Ramanathan G, ARKIVOC 2006 (x) 152
24. Yampolsky I V., Kislukhin A A., Armatov T T., Shcherbo D, Potapov V K., Lukyanov S, Lukyanov K A., Bioorg. Chem. 2008 36 96
25. Ivashkin P E., Yampolsky I V., Lukyanov K A., Russ. J. Bioorg. Chem. 2009 35 652
26. Bahadur L, Srivastava P, Semicond. Sci. Technol. 2004 19 531
27. Jain V, Rajbongshi B K., Mallajosyula A T., Bhattacharjya G, Iyer S S. K., Ramanathan G, Sol. Energy Mater. Sol. Cells 2008 92 1043
28. For reviews, see:, Nienhaus G U., Wiedenmann J, ChemPhysChem 2009 10 1369
29. Ribchester R R., Curr. Opin. Pharmacol. 2009 9 297
30. Bizzarri R, Serresi M, Luin S, Beltram F, Anal. Bioanal. Chem. 2009 393 1107
31. Muller-Taubenberger A, Anderson K I., Appl. Microbiol. Biotechnol. 2007 77 1
32. Hoffman R M., Nature 2005 5 796
33. Grigg R, Kemp J, Sheldrick G, Trotter J, J. Chem. Soc., Chem. Commun. 1978 109
34. For a review on nitrogen ylides, see:, Clark S J., In Nitrogen, Oxygen and Sulfur Ylide Chemistry Clark S J. Oxford University Press Oxford 2002 1-98
35. Escolano C, Duque M D., Vazques S, Curr. Org. Chem. 2007 11 741
36. Mangeney P, Tejero T, Alexakis A, Grosjean F, Normant J, Synthesis 1988 255
37. Cornforth J W., Cornforth R H., J. Chem. Soc. 1947 96
38. Lerestif J M., Perrocheau J, Tonnard F, Bazureau J.-P, Hamelin J, Tetrahedron 1995 51 6757
39. Dong J, Abulwerdi F, Baldridge A, Kowalik J, Solntsev K M., Tolbert L M., J. Am. Chem. Soc. 2008 130 14096
40. Kojima S, Hirano T, Niwa H, Ohashi M, Inouye S, Tsuji F I., Tetrahedron Lett. 1997 38 2875
41. Dong J, Solntsev K M., Poizat O, Tolbert L M., J. Am. Chem. Soc. 2007 129 10084
42. Ishi-i T, Iguchi R, Snip E, Ikeda M, Shinkai S, Langmuir 2001 17 58 25