1,3-Dipolar cycloaddition of azomethine ylide from Phtaloylimidophenylalanyl-2-hydroxymethylaziridine

Authors

  • Assia Keniche Laboratory of Organic chemistry, Natural Products and Analysis (COSNA). University of Tlemcen. P.O. Box 119 Tlemcen 13000/Algeria.
  • Wassila Drici Laboratory of Organic chemistry, Natural Products and Analysis (COSNA). University of Tlemcen. P.O. Box 119 Tlemcen 13000/Algeria.
  • Mohamed Zakaria Slimani Donostia International Physics Center. SGIker-RMN San Sebastián. Spain.
  • Abdelmoumen Mezrai Laboratory of Organic chemistry, Natural Products and Analysis (COSNA). University of Tlemcen. P.O. Box 119 Tlemcen 13000/Algeria.
  • Joseph Kajima Mulengi Laboratory of Organic chemistry, Natural Products and Analysis (COSNA). University of Tlemcen. P.O. Box 119 Tlemcen 13000/Algeria.

DOI:

https://doi.org/10.13171/mjc.2.4.2013.07.09.12

Abstract

Phtaloylimidophenylalanyl-2-hydroxymethylaziridine has been used as a starting material to yield azomethine ylide through thermal opening and was then involved into 1,3-dipolar cycloaddition reactions. Different five-membered adducts were obtained and were fully identified. The latter might be considered useful starting materials for further functionalization to provide novel compounds of biological interest.

References

W. Medjahed, A. Tabet Zatla, J. Kajima Mulengi, F. Z. Baba Ahmed, H. Merzouk, Tetrahedron Lett., 2004, 45, 1211-1213.

F. Z. Baba Ahmed, S. Bouanane, S. A. Merzouk, H. Merzouk, W. Medjahed, , J. Kajima Mulengi, J. Prost Pathol. Biol., 2008, 56, 137–142.

F. Z. Baba Ahmed, H. Merzouk, S. Bouanane, N. B. Benkalfat, S. A. Merzouk, J. Kajima Mulengi, M. Narce Ann. Toxicol Anal. 2010, DOI: 10.1051/ata/2010017. www.ata-journal.org.

R.B. Woodward, R. Hoffmann The conservation of orbital symmetry. p.57. Verlag Chemie Gmbh. Academic Press Inc. 1970.

J. Sisko, J. R. Henry, S. M. Weinreb J. Org. Chem. 1993, 58, 4945-4951

J. O. Baeg, C. Bensimon, H. Alper J. Am. Chem. Soc. 1995, 117, 4700-4701

M. Baumann, I.R. Baxendale, S. V. Ley, N. Nikbin Beilstein J. Org. Chem., 2011, 7, 442-495.

R. P. Robinson, E. R. Laird, K. M. Donahue, L. Lopresti-Morrow, P. G. Mitchell, M. R. Reese, L. M. Reeves, A. I. Rouch, E. J. Stam S. A. Yocum, Bioorg. Med. Chem. Lett., 2001, 11, 1211–1213.

Y. T. Reddy, K. R. Sekhar, N. Sasi, P. N. Reddy, M. L. Freeman, P. A. Crooks, Bioorg. Med. Chem. Lett, 2010, 20, 600–602.

M. H. Entezari, A. Asghari, F. Hadizadeh, Ultrasonics Sonochemistry, 2008, 15, 119–123.

W. J. Flosi, D. A. DeGoey, D. J. Grampovnik, H. Chen, L. L. Klein, T. Dekhtyar, S. Masse, K. C. Marsh, H. Mei M. Kemp, Bioorg. Med. Chem., 2006, 14, 6695–6712.

S. Cesarini, A. Spallarossa, A. Ranise, S. Schenone, C. Rosano, P. L. Colla, G. Sanna, B. Busonera, R. Loddo Eur. J. Med. Chem., 2009, 44, 1106-1118.

H. J. Patel, J. Sarra, F.Caruso, M. Rossi, U. Doshi, R. A. Stephani Bioorg. Med. Chem. Lett., 2006, 16, 4644–4647.

G. Pourceau, A. Myer, J. J. Vasseur, F. Morvan Methods Mol Biol, 2011, 751, 167-93.

J. A. Deyrup, W. A. Szabo J. Org. Chem. 1975, 40, 2048-2052.

G. P. Rizzi J. Org. Chem. 1970, 35, 2069-2072.

E. Vedejs, G.R Martinez J. Am. Chem. Soc. 1979, 101, 6452-6454.

W. H. Pearson, P. Stoy, Y. Mi J. Org. Chem. 2004, 69, 1919-1939.

G. Roussi, J. Zhang Tetrahedron 1991, 47, 5161- 5172.

(a) C. Na´jera, J. M. Sansano Angew. Chem., Int. Ed. 2005, 44, 6272–6276.

(b) C. Na´jera, J. M. Sansano Curr. Org. Chem. 2003, 7, 1105–1150.

S. Husinec, V. Savic Tetrahedron: Asymmetry 2005, 16, 2047–2061.

I. Coldham, R. Hufton Chem. Rev. 2005, 105, 2765–2809.

S. Kanemasa, Synlett 2002, 1371–1387.

K. V. Gothelf in Cycloaddition Reactions in Organic Synthesis. S. Kobayashi, K. A., Jørgensen Eds. Wiley- VCH: Weinheim, 2002; pp 211–245.

A. K. Yudin in Aziridines and Epoxides in Organic Synthesis Wiley-VCH Verlag GmbH & Co. KGaA 2006, pp56-59; pp 109-111 and references cited therein.

a) S. Takano, Y. Iwabuchi, K. Ogasawa J. Chem. Soc. Chem. Commun. 1988, 1204-1206; b) S. Takano, K. Samizu, K. Ogasawa Chem. Lett., 1990, 1239-1242.

R. B. Woodward, R. Hoffmann in The conservation of orbital symmetry. Verlag Chemie. Academic Press 1970, pp 38-48.

F. Zhang, H. Liu, Y. F. Li, H. M. Liu, Carbohydrate Research, 2010, 345, 839–843.

H. Zhang, Qi. Shen, L. Lu Tetrahedron Lett., 2011, 52, 349–351.

(a) R. Huisgen, W. Scheer, G. Szeimies, H. Huber Tetrahedron Lett. 1966,7, 397-404.

(b) R. Huisgen, W. Scheer, H. Huber J. Am. Chem. Soc. 1967, 89, 1753-1755.

H. Xie, J. Zhu, Z. Chen, S. Li, Y. Wu J. Org. Chem. 2010, 75, 7468-7471.

A. A. Raj, R. Raghunathan, M. R. Sridevi Kumari, N. Raman Bioorg. Med. Chem. 2003, 11, 407-419.

A. Padwa, H. Ku J. Org. Chem. 1979, 44, 255-261.

H. W. Heine, R. Peavy Tetrahedron Lett. 1965, 6, 3123-3126.

E. Erkizia, E. Aldaba, Y. Vara, A. Arrieta, H. Gornitza, F. P. Cossio Arkivoc 2005, IX, 189-199.

K. Amornraksa, D. Barr, G. Donegan, R. Grigg, P. Tatananukul, V. Shridharan Tetrahedron 1989, 45, 4649-4668.

A. Aizpurua, J.M. Palomo, Tetrahedron Lett. 1984, 25, 3365-3368.

Downloads

Published

2013-09-07

Issue

Section

Organic Chemistry