2007
DOI: 10.3390/12071482
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New “Green” Approaches to the Synthesis of Pyrazole Derivatives

Abstract: A novel approach to the synthesis of pyrazole derivatives from tosylhydrazones of α,β-unsaturated carbonyl compounds possessing a β-hydrogen is proposed, exploiting microwave (MW) activation coupled with solvent free reaction conditions. The cycloaddition was studied on three ketones (trans-4-phenyl-3-buten-2-one, β-ionone and trans-chalcone). The corresponding 3,5-disubstitued-1H-pyrazoles were obtained in high yields and after short reaction times. In order to simplify and point out the green chemistry featu… Show more

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Cited by 47 publications
(26 citation statements)
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“…Regardless of the existence of the so-called "specific" or "nonthermal" microwave effects, which is still the subject of an intense debate in the scientific community (33)(34)(35)(36)(37)(38), the peculiarities of microwave heating, such as its volumetric nature and its selectivity, are at the basis of unquestionable advantages in organic (39)(40)(41)(42)(43)(44) and inorganic (45)(46)(47)(48) chemistry, as well as in the materials science (49)(50)(51)(52) field.…”
Section: Numerical Simulation Resultsmentioning
confidence: 99%
“…Regardless of the existence of the so-called "specific" or "nonthermal" microwave effects, which is still the subject of an intense debate in the scientific community (33)(34)(35)(36)(37)(38), the peculiarities of microwave heating, such as its volumetric nature and its selectivity, are at the basis of unquestionable advantages in organic (39)(40)(41)(42)(43)(44) and inorganic (45)(46)(47)(48) chemistry, as well as in the materials science (49)(50)(51)(52) field.…”
Section: Numerical Simulation Resultsmentioning
confidence: 99%
“…Moreover the great advantages of the MW-assisted solvent-free synthetic protocol proposed here in a "green chemistry" context and as already demonstrated in previous work [72][73][74], should be emphasised.…”
Section: Mw Assisted Hydrothermal Clay Intercalationmentioning
confidence: 94%
“…Pyrazolines are prepared mainly by cyclization of chalcones with hydrazines 16,20,23 , from 1,3-dipolar cycloaddition reactions of nitrile imines to alkenes 26 by heating 27 or under microwaves 28 or from the cyclocondensation of hydrazines with 1,3-dihalides under MW irradiation 29 . Pyrazoles are synthesized mainly by the reaction of hydrazines with b-difunctional compounds 30 , from tosylhydrazones of a,b-unsaturated ketones under MW irradiation 31 and by 1,3-dipolar cycloaddition reactions of tosylhydrazone salts 32,33 or nitrile imines 25 with alkynes. In continuation to our work in the field of modified homo-N-nucleosides, we present here the reactions of 9-allyl-6-chloropurine with nitrile imines under MW irradiation and the replacement of chlorine by amines in the above products (Schemes 1 and 2).…”
Section: Introductionmentioning
confidence: 99%