Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2010(14): 2424-2436
DOI: 10.1055/s-0029-1218796
DOI: 10.1055/s-0029-1218796
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Efficient Synthesis of New 4-Arylideneimidazolin-5-ones Related to the GFP Chromophore by 2+3 Cyclocondensation of Arylideneimines with Imidate Ylides
Further Information
Received
22 December 2009
Publication Date:
20 May 2010 (online)
Publication History
Publication Date:
20 May 2010 (online)
![](https://www.thieme-connect.de/media/synthesis/201014/lookinside/thumbnails/10.1055-s-0029-1218796-1.jpg)
Abstract
A 2+3 condensation of a wide assortment of Schiff bases, prepared from aromatic aldehydes and primary amines, with methyl 2-(1-ethoxyethylideneamino)acetate allows convenient access to an extensive family of substituted 4-arylideneimidazolin-5-one analogues of the green fluorescent protein (GFP) chromophore.
Key words
4-arylideneimidazolin-5-one - azomethine ylide - Schiff bases - heterocycle - 2+3 cycloaddition
- 1
Tonge PJ.Meech SR. 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 SR.Jayaraj N.Ramamurthy V.Tolbert LM. J. Am. Chem. Soc. 2010, 132: 1498 - 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).
-
5a
Erlenmeyer E. Justus Liebigs Ann. Chem. 1893, 275: 1 -
5b
Plöchl J. Ber. Dtsch. Chem. Ges. 1883, 16: 2815 - The correct, azalactone structure of the reaction product came later, see:
-
5c
Erlenmeyer E. Ber. Dtsch. Chem. Ges. 1900, 33: 2036 -
5d
Kropp W.Decker H. Ber. Dtsch. Chem. Ges. 1909, 42: 1184 -
6a
Williams DL.Ronzio AR. J. Am. Chem. Soc. 1946, 68: 647 -
6b
Islam AM.Khalil AM.Abd El-Gawad II. Aust. J. Chem. 1973, 26: 827 -
6c
Badr MZ.El-Sherief HAH.Tadros ME. Bull. Chem. Soc. Jpn. 1982, 55: 2267 -
6d
Islam AM.Khalil AM.El-Houseni MS. Aust. J. Chem. 1973, 26: 1701 -
7a
He X.Bell AF.Tonge PJ. Org. Lett. 2002, 4: 1523 -
7b
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 - 8
Kojima S.Okhawa H.Hirano T.Maki S.Niwa H.Ohashi M.Inouye S.Tsui FI. Tetrahedron Lett. 1998, 5239 -
9a
Kawasaki A.Maekawa K.Kubo K.Igarashi T.Sakurai T. Tetrahedron 2004, 60: 9517 -
9b
Wu L.Burgess K. J. Am. Chem. Soc. 2008, 130: 4089 -
9c
Lerestif JM.Bazureau JP.Hamelin J. Tetrahedron Lett. 1993, 4639 -
9d
Devasia G. Tetrahedron Lett. 1976, 571 -
9e
Niwa H.Inouye S.Hirano T.Matsuno T.Kojima S.Kubota M.Ohashi M.Tsui FI. Proc. Natl. Acad. Sci. U.S.A. 1996, 93: 13617 -
9f
Oumouch S.Bourotte M.Schmitt M.Bourguignon J.-J. Synthesis 2005, 25 -
10a
Bhattacharjya G.Agasti SS.Ramanathan G. ARKIVOC 2006, (x): 152 -
10b
Yampolsky IV.Kislukhin AA.Armatov TT.Shcherbo D.Potapov VK.Lukyanov S.Lukyanov KA. Bioorg. Chem. 2008, 36: 96 - 11
Ivashkin PE.Yampolsky IV.Lukyanov KA. Russ. J. Bioorg. Chem. 2009, 35: 652 -
12a
Bahadur L.Srivastava P. Semicond. Sci. Technol. 2004, 19: 531 -
12b
Jain V.Rajbongshi BK.Mallajosyula AT.Bhattacharjya G.Iyer SSK.Ramanathan G. Sol. Energy Mater. Sol. Cells 2008, 92: 1043 - For reviews, see:
-
13a
Nienhaus GU.Wiedenmann J. ChemPhysChem 2009, 10: 1369 -
13b
Ribchester RR. Curr. Opin. Pharmacol. 2009, 9: 297 -
13c
Bizzarri R.Serresi M.Luin S.Beltram F. Anal. Bioanal. Chem. 2009, 393: 1107 -
13d
Muller-Taubenberger A.Anderson KI. Appl. Microbiol. Biotechnol. 2007, 77: 1 -
13e
Hoffman RM. Nature 2005, 5: 796 - 14
Grigg R.Kemp J.Sheldrick G.Trotter J. J. Chem. Soc., Chem. Commun. 1978, 109 - For a review on nitrogen ylides, see:
-
15a
Clark SJ. In Nitrogen, Oxygen and Sulfur Ylide ChemistryClark SJ. Oxford University Press; Oxford: 2002. p.1-98 -
15b
Escolano C.Duque MD.Vazques S. Curr. Org. Chem. 2007, 11: 741 - 16
Mangeney P.Tejero T.Alexakis A.Grosjean F.Normant J. Synthesis 1988, 255 -
17a
Cornforth JW.Cornforth RH. J. Chem. Soc. 1947, 96 -
17b
Lerestif JM.Perrocheau J.Tonnard F.Bazureau J.-P.Hamelin J. Tetrahedron 1995, 51: 6757 - 18
Dong J.Abulwerdi F.Baldridge A.Kowalik J.Solntsev KM.Tolbert LM. J. Am. Chem. Soc. 2008, 130: 14096 - 19
Kojima S.Hirano T.Niwa H.Ohashi M.Inouye S.Tsuji FI. Tetrahedron Lett. 1997, 38: 2875 - 20
Dong J.Solntsev KM.Poizat O.Tolbert LM. J. Am. Chem. Soc. 2007, 129: 10084 - 21
Ishi-i T.Iguchi R.Snip E.Ikeda M.Shinkai S. Langmuir 2001, 17: 5825