Reaction of Nitrilimines with 2-Aminopicoline, 3-Amino-1,2,4-Triazole, 5-Aminotetrazole and 2-Aminopyrimidine
Author(s)
Rami Y. Morjan1,
Basam S. Qeshta1,
Hussein T. Al-Shayyah1,
John M. Gardiner2,
Basam A. Abu-Thaher1,
Adel M. Awadallah1*
Affiliation(s)
1 Department of Chemistry, Islamic University of Gaza, Gaza, Palestine. 2 Manchester Institute of Biotechnology, School of Chemistry and EPS, The University of Manchester, Manchester, UK.
1 Department of Chemistry, Islamic University of Gaza, Gaza, Palestine. 2 Manchester Institute of Biotechnology, School of Chemistry and EPS, The University of Manchester, Manchester, UK.
ABSTRACT
The reaction of picoline derivatives 3-6 with hydrazonoylhalide 1a produced imidazo[1,2-a]pyridines 7-10, while the reaction of the same picoline derivatives with hydrazonoylhalide 1b afforded imidazo[1,2-a]pyridine-2-ones 11-13. The reaction of 1b, c with 3-amino-1,2,4-triazole 14 produced the acyclic adducts 18 and 19, respectively. Reaction of 1b, 1c with 5-aminotetrazole 20 produced the acyclic products 23 and 24, respectively. Finally, the reaction of 1b with 4, 6-dimethyl-2-aminopyrimidine 27 afforded compound 29 rather than its isomeric structure 28. The structure of the products was confirmed by the different spectroscopic analytical methods including IR, MS, 1HNMR and 13CNMR.
The reaction of picoline derivatives 3-6 with hydrazonoylhalide 1a produced imidazo[1,2-a]pyridines 7-10, while the reaction of the same picoline derivatives with hydrazonoylhalide 1b afforded imidazo[1,2-a]pyridine-2-ones 11-13. The reaction of 1b, c with 3-amino-1,2,4-triazole 14 produced the acyclic adducts 18 and 19, respectively. Reaction of 1b, 1c with 5-aminotetrazole 20 produced the acyclic products 23 and 24, respectively. Finally, the reaction of 1b with 4, 6-dimethyl-2-aminopyrimidine 27 afforded compound 29 rather than its isomeric structure 28. The structure of the products was confirmed by the different spectroscopic analytical methods including IR, MS, 1HNMR and 13CNMR.
Cite this paper
Morjan, R. , Qeshta, B. , Al-Shayyah, H. , Gardiner, J. , Abu-Thaher, B. and Awadallah, A. (2014) Reaction of Nitrilimines with 2-Aminopicoline, 3-Amino-1,2,4-Triazole, 5-Aminotetrazole and 2-Aminopyrimidine. International Journal of Organic Chemistry, 4, 201-207. doi: 10.4236/ijoc.2014.43023.
Morjan, R. , Qeshta, B. , Al-Shayyah, H. , Gardiner, J. , Abu-Thaher, B. and Awadallah, A. (2014) Reaction of Nitrilimines with 2-Aminopicoline, 3-Amino-1,2,4-Triazole, 5-Aminotetrazole and 2-Aminopyrimidine. International Journal of Organic Chemistry, 4, 201-207. doi: 10.4236/ijoc.2014.43023.
References
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http://dx.doi.org/10.3390/molecules13010170 [9] El-Abadelah, M.M., Hussein A.Q. and Thaher, B. (1991) Heterocycles from Nitrile Imines. Part IV. Chiral 4,5-Dihydro1,2,4-Triazin-6-Ones. Heterocycles, 32, 1879-1895.
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http://dx.doi.org/10.1002/jhet.5570200326 [12] Graf, H. and Klebe, G. (2006) 3-Aroyl-1-Aryl-1H-[1,2,4]Triazolo[3,4-c]-1,2,4-Triazole, Untersuchung des Bildungswegs durch Rontgenstrukturanalyse und Molecular Modelling. Chemische Berichte, 120, 965-977.
http://dx.doi.org/10.1002/cber.19871200614
[1] Padwa, A. (1984) 1,3-Diploar Cycloaddition Chemistry. Wiley, New York. [2] Ferwanah, A.R.S. and Awadallah, A.M. (2005) Reaction of Nitrilimines and Nitrile Oxides with Hydrazines, Hydrazones and Oximes. Molecules, 10, 492-507.
http://dx.doi.org/10.3390/10020492 [3] Thaher, B. (2003) Synthesis and Characterization of Some New Substituted Imidazo[1,2-a]Pyridines. Abhath Al-Yarmouk Journal (Series of Natural Studies), 12, 555-561. [4] Thaher, B. (2005) Synthesis of Some New Substituted Imidazo(1,2-a)Pyrazines. The Islamic University Journal (Series of Natural Studies and Engineering), 13, 109-115. [5] Thaher, B. (2006) Synthesis of Some New Substituted Imidazo(1,2-a)Pyridines and Their 2-One Derivatives. The Islamic University Journal (Series of Natural Studies and Engineering), 14, 31-38. [6] Awadallah, A.M., Seppelt, K. and Shorafa, H. (2006) Synthesis and X-Ray Crystal Structure of Pyrrolo[1,2-a]Benzimidazoles. Tetrahedron, 62, 7744-7746.
http://dx.doi.org/10.1016/j.tet.2006.05.071 [7] Elwan N. (2004) A Facile Synthesis of Pyrrolo[1,2-a]Benzimidazoles and Pyrazolo[3,4:4,3’]Pyrrolo[1,2-a]Benzimi-dazole Derivatives. Tetrahedron, 60, 1161-1166.
http://dx.doi.org/10.1016/j.tet.2003.11.068 [8] Awadallah, A.M. and Zahra J. (2008). Reaction of Nitrilimines with 2-Substituted Aza-Heterocycles. Synthesis of Pyrrolo[1,2-a]Pyridine and Pyrimido[2,1-d]1,2,3,5-Tetrazine. Molecules, 13, 170-176.
http://dx.doi.org/10.3390/molecules13010170 [9] El-Abadelah, M.M., Hussein A.Q. and Thaher, B. (1991) Heterocycles from Nitrile Imines. Part IV. Chiral 4,5-Dihydro1,2,4-Triazin-6-Ones. Heterocycles, 32, 1879-1895.
http://dx.doi.org/10.3987/COM-90-5637 [10] Shawali, A.S. (1993) Reactions of Heterocyclic Compounds with Nitrilimines and Their Precursors. Chemical Reviews, 93, 2731-2777.
http://dx.doi.org/10.1021/cr00024a007 [11] Abdelhamid, A.O., Hassaneen, H.M., Shawaki, A.S. and Pārkānyāi, C. (1983) Reactions of α-Ketohydrazidoyl Halides with Some Heterocyclic Amines. Facile Synthesis of Arylazo Derivatives of Fused Heterocycles with a Bridgehead Nitrogen Atom. Journal of Heterocyclic Chemistry, 20, 639-643.
http://dx.doi.org/10.1002/jhet.5570200326 [12] Graf, H. and Klebe, G. (2006) 3-Aroyl-1-Aryl-1H-[1,2,4]Triazolo[3,4-c]-1,2,4-Triazole, Untersuchung des Bildungswegs durch Rontgenstrukturanalyse und Molecular Modelling. Chemische Berichte, 120, 965-977.
http://dx.doi.org/10.1002/cber.19871200614