2003
DOI: 10.3390/80800642
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Microwave-Assisted Synthesis of Some 3,5-Arylated 2-Pyrazolines

Abstract: Condensation of 2-acetylnaphthalene with benzaldehydes under microwave irradiation affords chalcones which undergo facile and clean cyclizations with hydrazines RNHNH2 (R= H, Ph, Ac) to afford 3,5-arylated 2-pyrazolines in quantitative yields, also under microwave irradiation and in the presence of dry AcOH as cyclizing agent. The results obtained indicate that, unlike classical heating, microwave irradiation results in higher yields, shorter reaction times (2-12 min.) and cleaner reactions.

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Cited by 85 publications
(43 citation statements)
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“…Chalcones are a,b-unsaturated ketones which constitute an important group of natural products that serve as precursors for the synthesis of various heterocyclic compounds like pyrimidines, imidazoles, 1) pyrazoles, 2) 2-pyrazolines 3,4) and flavonoids. 5,6) Chalcones, either natural or synthetic, are known to exhibit various biological activities such as anti-inflammatory, 7,8) antifungal, [9][10][11][12] antioxidant, [13][14][15][16] antimalarial, [17][18][19][20] antituberculosis, 21) analgesic, 22) anti-human immunodeficiency virus (HIV) 23) and antitumor activities.…”
mentioning
confidence: 99%
“…Chalcones are a,b-unsaturated ketones which constitute an important group of natural products that serve as precursors for the synthesis of various heterocyclic compounds like pyrimidines, imidazoles, 1) pyrazoles, 2) 2-pyrazolines 3,4) and flavonoids. 5,6) Chalcones, either natural or synthetic, are known to exhibit various biological activities such as anti-inflammatory, 7,8) antifungal, [9][10][11][12] antioxidant, [13][14][15][16] antimalarial, [17][18][19][20] antituberculosis, 21) analgesic, 22) anti-human immunodeficiency virus (HIV) 23) and antitumor activities.…”
mentioning
confidence: 99%
“…The magnitude of the process energy that gives the highest yield is 8.4 kJ. The use of microwave radiation was also performed by Azarifar [15] for condensation reaction yielding several products with 300 watt power for several minutes and 80-95% yield. However, the effect of energy does not have an impact on product purity based on HPLC data.…”
Section: Synthesis Process Conditions Asymmetric Curcumin Analoguesmentioning
confidence: 99%
“…18) Condensation of acetylarenes with benzaldehydes under microwave irradiation affords [80] chalcones which undergo facile and clean cyclizations with hydrazines (RNHNH 2 , R=H, Ph, Ac) to afford 3,5-arylated 2-pyrazolines in quantitative yields, also under microwave irradiation and in the presence of dry AcOH as cyclizing agent. This is actually an example of Claisen-Smith reaction under MW irradiation.…”
Section: Microwave Assisted Organic Synthesismentioning
confidence: 99%