Naser FOROUGHIFAR, Akbar Mobinikhaledi And Sattar EBRAHIMI, Sattar EBRAHIMI

A simple and efficient procedure for synthesis of optically active 1,3,4-oxadiazole derivatives containing L-amino acid moieties

Some new unsymmetrical and optically active 2,5-disubstituted 1,3,4-oxadiazoles 5a-j were efficiently synthesized by cyclization reaction of diacylhydrazides 4a-j. The synthesis of the title compounds was achieved by the reaction of acyl hydrazides 3a-b and N-phetaloyl-L-amino acids 1a-e in the presence of the phosphoroxy chloride (POCl3) as an anhydrous reagent.

Anahtar Kelimeler:

N-phetaloyl-L-amino acid, 1, 3, 4-oxadiazole, diacylhydrazide, pyridoyl hydrazide, phosphoroxy chloride

A simple and efficient procedure for synthesis of optically active 1,3,4-oxadiazole derivatives containing L-amino acid moieties

Keywords:

N-phetaloyl-L-amino acid, 1, 3, 4-oxadiazole, diacylhydrazide, pyridoyl hydrazide, phosphoroxy chloride,

PDF

___

We synthesized some N-phetaloyl-L-amino acylchlorides having a free terminal carboxyl function, which can react with pyridoyl hydrazides at room temperature to give the intermediates 4a-j. Then these intermediates are cyclized to 5a-j at room temperature. This reaction may be useful for combinational synthesis of type 5 compounds having various R and Ar substituents with a view to test for biological activities. Shawali, A. S.; Abdallah, M. A.; Zayed, M. E. M. Eur. J. Med. Chem. 2009, 44, 2106-2112.
Lokanatha Rai, K. M.; Linganna, N. Farmaco 2000, 55 , 389-392.
Akhter, M.; Husain, A.; Azad, B.; Ajmal, M. Eur. J. Med. Chem. 2009, 44, 2372-2378.
Sheriﬀ, A. F.; Hayam M. A.; Ashour, R. H. A.; Razik, A. El; Fattah H. A. El; Fattah, A. El N.; Nagwa, El-D. Bioorg. Med. Chem. 2009, 17, 2410-2422.
Tan, T. M. C.; Chen, Y.; Kong, K. H.; Bai, J.; Li, Y.; Lim, G. S.; Ang, T. H.; Lam, Y. Antiviral Research 2006, , 7-14.
Warrener, R. N. Eur. J. Org. Chem. 2000, 20, 3363-3380.
Brog, S.; Vollinga, R. C.; Labarre, M.; Payza, K.; Luthman L.; Terenius, K. J. Med. Chem. 1999, 42, 4331-4342.
ShaŞee, A.; Naimi, E.; Mansobi, P.; Foroumadi A.; Shekari, M. J. Heterocycl. Chem. 1995. 32, 1235-1239.
He, D.-H.; Zhu, Y.-C.; Yang, Z.-R.; Hu A.-X.; Cao, G. Turk. J. Chem., 2009 33, 1-5.
Sharma, S.; Srivastava, V. K; Kumar, A. Eur. J. Med. Chem. 2002, 37, 689-697.
Liras, S.; Allen M. P.; Segelestin, B. E. Synth. Commun. 2000, 30, 437-443.
Rigo, B.; Caullez, P.; Fasseur, D.; Couturier, D. Synth. Commun. 1989, 19, 2321-2335.
Brain, C. T.; Paul, J. M.; Loong Y.; Oakley, P. J. Tetrahedron Lett. 1999, 40, 3275-3278.
Bentiss, H.; Lagrenee, M. J. Heterocycl. Chem. 1999, 36, 1029-1032.
Bing, Y. J.; Leungb, L. M.; Menglian, G. Tetrahedron Letters 2004, 45, 6361-6363.
Foroughifar, N.; Mobinikhaledi, A.; Ebrahimi, S.; Bodaghi Fard, M. A.; Moghanian, M. J. Chin. Chem. Soc., 2009, , 1043-1047
Zamani, Kh.; Faghihi, Kh.; Ebrahimi, S. Turk. J. Chem., 2005, 29, 171-175.