IJOC  Vol.4 No.2 , June 2014
A Modified Method for the Synthesis of Tetradentate Ligand Involving Peptide Bond
Abstract: In view of the importance of picolinic acid (Pa) in preventing cell growth and arresting cell cycle, attempts were made to design, synthesize and characterize two new Pa based tetradentate ligands (DPPTR and DPPTY) with a modified procedure. The procedure reported here avoids by-products and provides better yield and purity.
Cite this paper: Reddy, P. , Chandrashekar, R. , Shaik, H. and Satyanarayana, B. (2014) A Modified Method for the Synthesis of Tetradentate Ligand Involving Peptide Bond. International Journal of Organic Chemistry, 4, 122-134. doi: 10.4236/ijoc.2014.42014.

[1]   Han, S.-Y. and Kim, Y.-A. (2004) Recent Development of Peptide Coupling Reagents in Organic Synthesis. Tetrahedron, 60, 2447-2467.

[2]   Al berico, F. (2004) Developments in Peptide and Amide Synthesis. Current Opinion in Chemical Biology, 8, 211-221.

[3]   Bodanszky, M. and Bodansky, A. (1984) The Practice of Peptide Synthesis. Springer, New York.

[4]   Sheehan, J.C. and Hess, G.P. (1955) A New Method of Forming Peptide Bonds. Journal of the American Chemical Society, 17, 1067-1068.

[5]   Valuer, E. andBradley, M. (2009) Amide Bond Formation: Beyond the Myth of Coupling Reagents. The Royal Society of Chemistry, 38, 606-631.

[6]   Sheehan, J.C., Cruickshank, P.A. and Boshart, G.L. (1961) Convenient Synthesis of Water-Soluble Carbodiimides. The Journal of Organic Chemistry, 26, 2525-2528.

[7]   Himaja, M., Prathap, K.J., Mali, S.V. and Ramana, M.V. (2011) Synthesis Antibacterial and Insecticidal of a New Series of 4-(5-Methyl-1,2,4-triazolo[1,5-a]pyridine-7-ylamino)-N-(aryl)benzamides. Indian Journal of Hetero Cyclic Chemistry, 20, 317-320.

[8]   Brogly, L., Dappen, M., Thorsett, E. and Tucker, J. (2001) Amide Bond Formation Using HATU in High throughput Synthesis. Proceedings of the 222nd ACS Nation Meeting, Chicago, 26-30 August 2001, MEDI-112.

[9]   Xiao, Z., Yang, M.G., Li, P. and Percy, H. (2009) Synthesis of 3-Subbstited-4(3H)-Quinazolinones via HATU-Mediated Coupling of 4-Hydroxyquinazolines with Amines. Organic Letters, 11, 1421-1424.

[10]   Prasad, B., Sambarkar, A. and Patil, C. (2012) Synthesis of Amides from Acids and Using Coupling Reagents. Journal of Current Pharmaceutical Research, 10, 22-24.

[11]   Glunz, P.W. (2004) Preparation of Pyrrolo[1,2-a]Pyrimidinones as Coagulation Cascade Inhibitors. From PCT Int. Appl., WO2004002406 A2 20040108.

[12]   Joullie, M.M. and Lassen, K.M. (2010) Evolution of Amide Bond Formation. ARKIVOC, viii, 189-250.

[13]   Londregan, A.T., Storer, G., Wooten, C., Yang, X.J. and Warmus, J. (2009) An Improved Amide Coupling Procedure for the Synthesis of N-(Pyridin-2-yl)Amines. Tetrahedron Letters, 50, 1986-1988.

[14]   Tran, T.P., Mullins, P.B., am Ende, C.W. and Pettersson, M. (2013) Synthesis of Pyridopyrazine-1,6-Diones from 6-Hydroxypicolinic Acids via One-Pot Cou-pling/Cyclization Reaction. Organic Letters, 15, 642-645.

[15]   ChemBark. News, Analysis, and Commentary for the World of Chemistry & Chemical Research, Amide Bond Formation Using HATU.

[16]   Zhang, H.K., Zhang, X., Mao, B.Z., Li, Q. and He, Z.H. (2004) Alpha-Picolinic Acid, a Fungal Toxin and Mammal Apoptosis-Inducing Agent, Elicits Hypersensitive-Like Response and Enhances Disease Resistance in Rice. Cell Research, 14, 27-33.

[17]   Fulmer, G.R., Miller, A.J.M., Sherden, N.H., Gottlieb, H.E., Nundelman, A., Stoltz, B.M., Bercaw, J.E. and Goldberg, K.I. (2010) NMR Chemical Schifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deute-rated Solvents Relevant to the Organometallic Chemist. Organometallics, 29, 2176-2179.

[18]   Gottlieb, H.E., Kotlyar, V. and Nundelman, A. (1997) NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities. The Journal of Organic Chemistry, 62, 7512-7515.

[19]   Carpino, L.A. (1993) 1-Hydroxy-7-Azabenzotriazole. An Efficient Peptide Coupling Additive. Journal of the American Chemical Society, 115, 4397-4398.

[20]   Carpino, L.A., Imazuumi, H., El-Faham, A., Ferrer, F.J., Zhamg, C., Lee, Y., Foxmam, B.M., Heanklein, P., Hanay, C., Mugge, C., Wensahuh, H., Klose, J., Beyermanm, M. and Bienert, M. (2002) The Uronium/Guanidinium Peptide Coupling Reagents: Finally the True Uronium Salts. Angewandte Chemie International Edition, 41, 441-445.

[21]   Carpino, L.A., Imazumi, H., Foxman, B.M., Vela, M.J., Henklein, P., El-Faham, A., Klose, J. and Bienert, M. (2000) Comparison of the Effects of 5- and 6-HOAt on Model Peptide Coupling Reactions Relative to the Cases for the 4- and 7-Isomers. Organic Letters, 2, 2253-2256.

[22]   Nakamoto, K. (1978) Infrared and Raman Spectra of Inorganic and Coordination Compounds. 3rd Editon, John Wiley & Sons, New York, 228.

[23]   Mc Murray, J. (1992) Organic Chemistry. 3rd Edition, Cole Publishing Company, California, 814.