Efficient Synthesis of New 4-Arylideneimidazolin-5-ones
Related to the GFP Chromophore by 2+3 Cyclocondensation
of Arylideneimines with Imidate Ylides

Anthony Baldridge; Janusz Kowalik; Laren M. Tolbert

doi:10.1055/s-0029-1218796

PAPER

Efficient Synthesis of New 4-Arylideneimidazolin-5-ones Related to the GFP Chromophore by 2+3 Cyclocondensation of Arylideneimines with Imidate Ylides

Anthony Baldridge, Janusz Kowalik*, Laren M. Tolbert
School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332-0400, USA
Fax: +1(404)8947452; e-Mail: janusz.kowalik@chemistry.gatech.edu;

Abstract

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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

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References

<A NAME="RM06809SS-1">1</A> Tonge PJ. Meech SR. J. Photochem. Photobiol., A 2009, 205: 1

<A NAME="RM06809SS-2">2</A> Wu L. Burgess K. J. Am. Chem. Soc. 2008, 130: 4089

<A NAME="RM06809SS-3">3</A> 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

<A NAME="RM06809SS-4">4</A> 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).

<A NAME="RM06809SS-5A">5a</A> Erlenmeyer E. Justus Liebigs Ann. Chem. 1893, 275: 1

<A NAME="RM06809SS-5B">5b</A> Plöchl J. Ber. Dtsch. Chem. Ges. 1883, 16: 2815

The correct, azalactone structure of the reaction product came later, see:

<A NAME="RM06809SS-5C">5c</A> Erlenmeyer E. Ber. Dtsch. Chem. Ges. 1900, 33: 2036

<A NAME="RM06809SS-5D">5d</A> Kropp W. Decker H. Ber. Dtsch. Chem. Ges. 1909, 42: 1184

<A NAME="RM06809SS-6A">6a</A> Williams DL. Ronzio AR. J. Am. Chem. Soc. 1946, 68: 647

<A NAME="RM06809SS-6B">6b</A> Islam AM. Khalil AM. Abd El-Gawad II. Aust. J. Chem. 1973, 26: 827

<A NAME="RM06809SS-6C">6c</A> Badr MZ. El-Sherief HAH. Tadros ME. Bull. Chem. Soc. Jpn. 1982, 55: 2267

<A NAME="RM06809SS-6D">6d</A> Islam AM. Khalil AM. El-Houseni MS. Aust. J. Chem. 1973, 26: 1701

<A NAME="RM06809SS-7A">7a</A> He X. Bell AF. Tonge PJ. Org. Lett. 2002, 4: 1523

<A NAME="RM06809SS-7B">7b</A> 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

<A NAME="RM06809SS-8">8</A> Kojima S. Okhawa H. Hirano T. Maki S. Niwa H. Ohashi M. Inouye S. Tsui FI. Tetrahedron Lett. 1998, 5239

<A NAME="RM06809SS-9A">9a</A> Kawasaki A. Maekawa K. Kubo K. Igarashi T. Sakurai T. Tetrahedron 2004, 60: 9517

<A NAME="RM06809SS-9B">9b</A> Wu L. Burgess K. J. Am. Chem. Soc. 2008, 130: 4089

<A NAME="RM06809SS-9C">9c</A> Lerestif JM. Bazureau JP. Hamelin J. Tetrahedron Lett. 1993, 4639

<A NAME="RM06809SS-9D">9d</A> Devasia G. Tetrahedron Lett. 1976, 571

<A NAME="RM06809SS-9E">9e</A> 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

<A NAME="RM06809SS-9F">9f</A> Oumouch S. Bourotte M. Schmitt M. Bourguignon J.-J. Synthesis 2005, 25

<A NAME="RM06809SS-10A">10a</A> Bhattacharjya G. Agasti SS. Ramanathan G. ARKIVOC 2006, (x): 152

<A NAME="RM06809SS-10B">10b</A> Yampolsky IV. Kislukhin AA. Armatov TT. Shcherbo D. Potapov VK. Lukyanov S. Lukyanov KA. Bioorg. Chem. 2008, 36: 96

<A NAME="RM06809SS-11">11</A> Ivashkin PE. Yampolsky IV. Lukyanov KA. Russ. J. Bioorg. Chem. 2009, 35: 652

<A NAME="RM06809SS-12A">12a</A> Bahadur L. Srivastava P. Semicond. Sci. Technol. 2004, 19: 531

<A NAME="RM06809SS-12B">12b</A> Jain V. Rajbongshi BK. Mallajosyula AT. Bhattacharjya G. Iyer SSK. Ramanathan G. Sol. Energy Mater. Sol. Cells 2008, 92: 1043

For reviews, see:

<A NAME="RM06809SS-13A">13a</A> Nienhaus GU. Wiedenmann J. ChemPhysChem 2009, 10: 1369

<A NAME="RM06809SS-13B">13b</A> Ribchester RR. Curr. Opin. Pharmacol. 2009, 9: 297

<A NAME="RM06809SS-13C">13c</A> Bizzarri R. Serresi M. Luin S. Beltram F. Anal. Bioanal. Chem. 2009, 393: 1107

<A NAME="RM06809SS-13D">13d</A> Muller-Taubenberger A. Anderson KI. Appl. Microbiol. Biotechnol. 2007, 77: 1

<A NAME="RM06809SS-13E">13e</A> Hoffman RM. Nature 2005, 5: 796

<A NAME="RM06809SS-14">14</A> Grigg R. Kemp J. Sheldrick G. Trotter J. J. Chem. Soc., Chem. Commun. 1978, 109

For a review on nitrogen ylides, see:

<A NAME="RM06809SS-15A">15a</A> Clark SJ. In Nitrogen, Oxygen and Sulfur Ylide Chemistry Clark SJ. Oxford University Press; Oxford: 2002. p.1-98

<A NAME="RM06809SS-15B">15b</A> Escolano C. Duque MD. Vazques S. Curr. Org. Chem. 2007, 11: 741

<A NAME="RM06809SS-16">16</A> Mangeney P. Tejero T. Alexakis A. Grosjean F. Normant J. Synthesis 1988, 255

<A NAME="RM06809SS-17A">17a</A> Cornforth JW. Cornforth RH. J. Chem. Soc. 1947, 96

<A NAME="RM06809SS-17B">17b</A> Lerestif JM. Perrocheau J. Tonnard F. Bazureau J.-P. Hamelin J. Tetrahedron 1995, 51: 6757

<A NAME="RM06809SS-18">18</A> Dong J. Abulwerdi F. Baldridge A. Kowalik J. Solntsev KM. Tolbert LM. J. Am. Chem. Soc. 2008, 130: 14096

<A NAME="RM06809SS-19">19</A> Kojima S. Hirano T. Niwa H. Ohashi M. Inouye S. Tsuji FI. Tetrahedron Lett. 1997, 38: 2875

<A NAME="RM06809SS-20">20</A> Dong J. Solntsev KM. Poizat O. Tolbert LM. J. Am. Chem. Soc. 2007, 129: 10084

<A NAME="RM06809SS-21">21</A> Ishi-i T. Iguchi R. Snip E. Ikeda M. Shinkai S. Langmuir 2001, 17: 5825