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Enamines in Heterocyclic Synthesis: Route to Aminopyrazolopyrimidines and Arylpyrazolopyrimidiens Derivatives

Received: 20 February 2014    Accepted:     Published: 30 March 2014
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Abstract

An easy preparation of enaminonitrile derivatives, obtained by using a mixture of triethyl orthoformate and piperidine in DMF solution, and their transformation into new substituted azolopyrimidines is described. The one-step transformation was carried out under microwave irradiation and by classical heating methods. The use of microwave irradiation led to high conversion and shorter reaction times.

DOI 10.11648/j.mc.20140201.11
Published in Modern Chemistry (Volume 2, Issue 1, February 2014)
Page(s) 1-5
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

Pyrazolopyrimidines, Enamines, Aminopyrazole, Microwave Irradiation

References
[1] A. S. Shawali, M.A. Mosselhi, “Hydrazonoyl halides: Useful building blocks for the synthesis of arylazoheterocycles”; J. Heterocycl. Chem. 2003, 40, 725-746.
[2] B. Stanovnik, J. Svete, “The Synthesis Aplysinopsins, Meridianines, and Related Compounds” Mini-Reviews in Organic Chemistry 2005, 2, 211-224.
[3] A. Elassara, A. A. El-Khair, “Recent developments in the chemistry of enaminones”; Tetrahedron, 2003, 59, 8463-8480.
[4] J. G. Buchanan, D. Smith, R. Wightman, “C-Nucleoside studies-15: Synthesis of 3-β-D-arabinofuranosylpyrazoles and the D-arabinofuranosyl analogue of formycin”; Tetrahedron, 1984, 40, 119-123.
[5] A. F. Lewis, R. A. Long, L. W. Roti, L. B. Townsend,” Synthesis of 4-amino-3-(β-D-ribofuranosyl)pyrazole-5-carboxarnidc via ring fission of formycin derivatives and purification using high pressure liquid chromatography”; J. Heterocycl. Chem. 1976, 13, 1359-1361.
[6] S. A. S. Ghozlan, I. A. Abdelhamid, H. Gaber, M. H. Elnagdi, Studies with functionally substituted enamines: synthesis of new aminoazolo-pyrimidines and -1,2,4-triazines J. Chem. Res. 2004, 789-793.
[7] S. O. Abdallah, N. H. Metwally, H. F. Anwar, M. H. E1nagdi, Synthesis and chemical reactivity of 3-oxo-2-aryl hydrazonopropanenitriles J. Heterocycl. Chem. 2005, 42, 781-786.
[8] S. A. Raghunath, Y. Manjunatha, K. Rayappa, Synthesis, antimicrobial, and antioxidant activities of some new indole analogues containing pyrimidine and fused pyrimidine systems Med. Chem. Res. 2012, 21, 3809-3817.
[9] R. Bradbury, in A. T. Peters, H. S. Freeman, (Eds.), Advance in Color Chemistry Series, Vol. 3 Modern Colorants – Synthesis and Structure, Blackie Academic, London, 1995.
[10] K. Hunger, (Ed.) Industrial Dyes: Chemistry Properties, Applications, Wiley-VCH, Weinheim, 2003.
[11] D. M. Mingos, D. R. Baghurst, Tilden Lecture. Applications of microwave dielectric heating effects to synthetic problems in chemistry, Chem. Soc. Rev. 1991, 20, 1–47.
[12] A. K. Bose, M. S. Manhas, S. N. Gandguyly, A. H. Sharma, B. K. Banik, MORE Chemistry for Less Pollution: Applications for Process Development. Synthesis 2002, 1578-1591.
[13] E. S. Darwish, M. A. Abdelrahman, A. M. Salaheldin, Enamines in Heterocyclic Synthesis: A Novel Simple and Efficient Route to Condensed Pyridazines Z. Naturforsch. 2011, 66b, 597 – 602.
[14] A. M. Salaheldin, Cyanoacetylation of 5-Aminopyrazole: Synthesis of 2-(1-Aryl-4-substituted pyrazolo[3,4-d]pyrimidin-6-yl)acetonitrile Derivatives Z. Naturforsch. 2009, 64b, 840 – 846.
[15] A. M. Salaheldin, Enaminonitriles in Heterocyclic Synthesis: Novel Synthesis of 3-Aminopyrroles and Pyrrolo[3,2-d]pyrimidine Derivatives Z. Naturforsch. 2008, 63b, 564 – 570.
[16] M. Salaheldin, M. A. Al-Shiekh,” β-Enamino Esters in Heterocyclic Synthesis: Synthesis of Pyrazolone and Pyridinone Derivatives”; Molecules 2010, 15, 4359 – 4368.
[17] H. Y. Medrasi, M. A. Al-Sheikh, and A. M. Salaheldin, “Enaminonitriles in Heterocyclic Synthesis: A Route to 1,3-Diaryl-4-aminopyrazole Derivatives “Molecules 2013, 18, 535-544.
[18] M. H. E1nagdi, S. O. Abdallah, Reactions with the Arylhydrazones of some α-cyanoketones. J. Prakt. Chem. 1973, 315, 1009-1016.
[19] F. M. Manhi, S. E. Zayed, F. A. Ali and M. H. Elnagdi, Studies with Polyfunctionally Substituted Heterocycles: Novel Syntheses of Pyrido[4,3-d]pyridazines and of Pyrido[3,4-d]pyridazines. Coll. Czech. Chem. Commun. 1992, 57, 1770-1774.
[20] M. A. Safan, F. M. A. El-Toweel, A. G. A. Elagemy, M. H. Elnagdi, Studies on Cinnamonitriles: The Reaction of Cinnamonitriles with Cyclopentanone. Liebigs Ann. Chem. 1989, 935-936.
[21] Salaheldin, A.M.; Alphy, M. A.; “Studies with Enaminonitriles: Synthesis and Chemical Reactivity of 2-Phenyl -3-Piperidin-1-yl Acrylonitrile under Microwave Heating”, J. Heterocycl. Chem., 2008, 45, 307.
[22] Almazroa, S.; Salaheldin, A.M.; Elnagdi, M.H.; “Studies with enaminones: The reaction of enaminones with aminoheterocycles. A route to azolopyrimidines, azolopyridines and quinolines”. J. Heterocycl. Chem. 2004, 41, 267-272.
Author Information
  • Department of Chemistry, Sciences faculty for Girls, King Abdulaziz University, Jeddah, Jeddah, KSA

  • Department of Chemistry, College of Applied Sciences, Umm Al-Qura University, Makkah, KSA

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    Hanadi Yousef. Medrasi, Abdellatif Mohamed Salaheldin. (2014). Enamines in Heterocyclic Synthesis: Route to Aminopyrazolopyrimidines and Arylpyrazolopyrimidiens Derivatives. Modern Chemistry, 2(1), 1-5. https://doi.org/10.11648/j.mc.20140201.11

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    ACS Style

    Hanadi Yousef. Medrasi; Abdellatif Mohamed Salaheldin. Enamines in Heterocyclic Synthesis: Route to Aminopyrazolopyrimidines and Arylpyrazolopyrimidiens Derivatives. Mod. Chem. 2014, 2(1), 1-5. doi: 10.11648/j.mc.20140201.11

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    AMA Style

    Hanadi Yousef. Medrasi, Abdellatif Mohamed Salaheldin. Enamines in Heterocyclic Synthesis: Route to Aminopyrazolopyrimidines and Arylpyrazolopyrimidiens Derivatives. Mod Chem. 2014;2(1):1-5. doi: 10.11648/j.mc.20140201.11

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  • @article{10.11648/j.mc.20140201.11,
      author = {Hanadi Yousef. Medrasi and Abdellatif Mohamed Salaheldin},
      title = {Enamines in Heterocyclic Synthesis: Route to Aminopyrazolopyrimidines and Arylpyrazolopyrimidiens Derivatives},
      journal = {Modern Chemistry},
      volume = {2},
      number = {1},
      pages = {1-5},
      doi = {10.11648/j.mc.20140201.11},
      url = {https://doi.org/10.11648/j.mc.20140201.11},
      eprint = {https://download.sciencepg.com/pdf/10.11648.j.mc.20140201.11},
      abstract = {An easy preparation of enaminonitrile derivatives, obtained by using a mixture of triethyl orthoformate and piperidine in DMF solution, and their transformation into new substituted azolopyrimidines is described. The one-step transformation was carried out under microwave irradiation and by classical heating methods. The use of microwave irradiation led to high conversion and shorter reaction times.},
     year = {2014}
    }
    

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    T1  - Enamines in Heterocyclic Synthesis: Route to Aminopyrazolopyrimidines and Arylpyrazolopyrimidiens Derivatives
    AU  - Hanadi Yousef. Medrasi
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    AB  - An easy preparation of enaminonitrile derivatives, obtained by using a mixture of triethyl orthoformate and piperidine in DMF solution, and their transformation into new substituted azolopyrimidines is described. The one-step transformation was carried out under microwave irradiation and by classical heating methods. The use of microwave irradiation led to high conversion and shorter reaction times.
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