Enamines in Heterocyclic Synthesis: Route to Aminopyrazolopyrimidines and Arylpyrazolopyrimidiens Derivatives
Volume 2, Issue 1, February 2014, Pages: 1-5
Received: Feb. 20, 2014;
Published: Mar. 30, 2014
Views 3570 Downloads 211
Hanadi Yousef. Medrasi, Department of Chemistry, Sciences faculty for Girls, King Abdulaziz University, Jeddah, Jeddah, KSA
Abdellatif Mohamed Salaheldin, Department of Chemistry, College of Applied Sciences, Umm Al-Qura University, Makkah, KSA
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.
Hanadi Yousef. Medrasi,
Abdellatif Mohamed Salaheldin,
Enamines in Heterocyclic Synthesis: Route to Aminopyrazolopyrimidines and Arylpyrazolopyrimidiens Derivatives, Modern Chemistry.
Vol. 2, No. 1,
2014, pp. 1-5.
A. S. Shawali, M.A. Mosselhi, “Hydrazonoyl halides: Useful building blocks for the synthesis of arylazoheterocycles”; J. Heterocycl. Chem. 2003, 40, 725-746.
B. Stanovnik, J. Svete, “The Synthesis Aplysinopsins, Meridianines, and Related Compounds” Mini-Reviews in Organic Chemistry 2005, 2, 211-224.
A. Elassara, A. A. El-Khair, “Recent developments in the chemistry of enaminones”; Tetrahedron, 2003, 59, 8463-8480.
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.
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.
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.
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.
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.
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.
K. Hunger, (Ed.) Industrial Dyes: Chemistry Properties, Applications, Wiley-VCH, Weinheim, 2003.
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.
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.
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.
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.
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.
M. Salaheldin, M. A. Al-Shiekh,” β-Enamino Esters in Heterocyclic Synthesis: Synthesis of Pyrazolone and Pyridinone Derivatives”; Molecules 2010, 15, 4359 – 4368.
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.
M. H. E1nagdi, S. O. Abdallah, Reactions with the Arylhydrazones of some α-cyanoketones. J. Prakt. Chem. 1973, 315, 1009-1016.
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.
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.
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.
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.