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Green One Pot Solvent-Free Synthesis of Pyrano[2,3-c]-Pyrazoles and Pyrazolo[1,5-a]Pyrimidines
Chemistry Department, Faculty of Science, University of Kuwait, P.O. Box 5969, Safat, 13060 Kuwait
Chemistry Department, Faculty of Science, Cairo University, Giza, 12613, Egypt
* Author to whom correspondence should be addressed.
Received: 26 July 2010; in revised form: 13 August 2010 / Accepted: 26 August 2010 / Published: 20 September 2010
Abstract: Pyrano[2,3-c]pyrazoles are obtained via mixing ethyl acetoacetate, hydrazine hydrate, aldehydes or ketones and malononitrile in the absence of solvent. These same products were also obtained by reacting arylidenemalononitriles 3 with 3-methyl-2-pyrazolin-5-ones. NOE difference experiments confirmed that these products exist solely in the 2H form. Similar treatments of 3-amino-2-pyrazolin-5-one with arylidene-malononitrile afforded adduct 6. Similarly mixing ethyl cyanoacetate, hydrazine hydrate, aldehydes, with malononitrile gave the same product 6. A novel synthesis of 4-oxo-4H-pyrano[2,3-c]pyrazole (8) could be achieved via reacting 3-methyl-2-pyrazolin-5-one with a mixture of cyanoacetic acid and acetic anhydride. Similar treatment of 3-aminopyrazole 11 with the benzylidene-malononitrile produced the pyrazolo[2,3-a]pyrimidines 12a,b.
Keywords: pyranopyrazole; multi-component synthesis; aminopyrazolinone; pyrazolo[1,5-a]pyrimidine; cyanoacetic acetic anhydride; NOE difference experiments
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Al-Matar, H.M.; Khalil, K.D.; Adam, A.Y.; Elnagdi, M.H. Green One Pot Solvent-Free Synthesis of Pyrano[2,3-c]-Pyrazoles and Pyrazolo[1,5-a]Pyrimidines. Molecules 2010, 15, 6619-6629.
Al-Matar HM, Khalil KD, Adam AY, Elnagdi MH. Green One Pot Solvent-Free Synthesis of Pyrano[2,3-c]-Pyrazoles and Pyrazolo[1,5-a]Pyrimidines. Molecules. 2010; 15(9):6619-6629.
Al-Matar, Hamad M.; Khalil, Khaled D.; Adam, Aisha Y.; Elnagdi, Mohamed H. 2010. "Green One Pot Solvent-Free Synthesis of Pyrano[2,3-c]-Pyrazoles and Pyrazolo[1,5-a]Pyrimidines." Molecules 15, no. 9: 6619-6629.