<i>L</i>‐Proline Catalyzed Solvent‐Free Knoevenagel Condensation for the Synthesis of 3‐Substituted Coumarins

Karade, Nandkishor N.; Gampawar, Sumit V.; Shinde, Sandeep V.; Jadhav, Wamanrao N.

doi:10.1002/cjoc.200790311

Cited by 55 publications

(28 citation statements)

References 35 publications

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“…Compounds b1-3 were synthesized from salicylaldehydes by the literature [31], then they were brominated with molecular bromine in chloroform. 2-amino-4-(R 1 -coumarin-3-yl)thiazoles (d1-3) were obtained by the reactions of c1-3 with thiourea.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, antioxidant and anticholinesterase activities of novel coumarylthiazole derivatives

Kurt

Gazioğlu

Sönmez

et al. 2015

Bioorganic Chemistry

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Section: Chemistrymentioning

confidence: 99%

Synthesis, antioxidant and anticholinesterase activities of novel coumarylthiazole derivatives

Kurt

Gazioğlu

Sönmez

et al. 2015

Bioorganic Chemistry

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“…The synthetic plan to obtain the intended coumarins is depicted in Scheme 3. Coumarins 1 – 3 and 6 – 8 were obtained by Knoevenagel reactions between specific aromatic aldehydes and β‐ketoesters ( 1 – 3 , 6 , and 7 ) or malonic acid ( 8 ) employing the conditions described by Karade et al . or Vazquez‐Rodriguez .…”

Section: Resultsmentioning

confidence: 99%

In vitro and in vivo trypanocidal activities of 8‐methoxy‐3‐(4‐nitrobenzoyl)‐6‐propyl‐2H‐cromen‐2‐one, a new synthetic coumarin of low cytotoxicity against mammalian cells

et al. 2018

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Natural and synthetic coumarins have been described as prototypes of new drug candidates against Chagas' disease. During a typical screening with new compounds, we observed the potential of a new synthetic nitrobenzoylcoumarin (1) as trypanocidal against Trypanosoma cruzi epimastigotas. Then, we decided to prepare and evaluate a set of analogues from 1 to check the major structural requirements for trypanocidal activity. The structural variations were conducted in six different sites on the original compound and the best derivative (3) presented activity (IC 28 ± 3 μM) similar to that of benznidazole (IC 25 ± 10 μM). The enhancement of trypanocidal activity was conditioned to a change in the side chain at C6 (allyl to n-propyl group) and the preservation of coumarin nucleus and the nitrobenzoyl group at C3. Exposure of 3 to H9C2 cells showed low toxicity (CC > 200 μM) and its activity on T. cruzi amastigotes (IC 13 ± 0.3 μM) encouraged us to perform an evaluation of its potential when given orally to mice infected with trypomastigote forms. Derivative 3 was able to reduce parasitemia when compared to the group of untreated animals. Taken together, these results show the potential therapeutic application of the synthetic coumarins.

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“…Using our catalytic device, 3-cyanocoumarin (15) and 3-(ethoxycarbonyl)coumarin (16) were obtained in 94% and 30% yields, respectively (Table 1, entries 3 and 4). The moderate conversion for the synthesis of 16, when compared to 15, is ascribed to the lower reactivity of diethyl malonate (11) in comparison to ethyl cyanoacetate (10) [36].…”

Section: Resultsmentioning

confidence: 99%

Piperazine-Containing Polymer Brush Layer as Supported Base Catalyst in a Glass Microreactor

Munirathinam¹,

Huskens²,

Verboom³

2014

J Flow Chem

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The covalent attachment of piperazine onto the inner walls of a microreactor using glycidyl methacrylate polymer brushes has been demonstrated. The piperazine-containing polymer brushes were first grown on a flat silicon oxide surface and were characterized by contact angle, Fourier transform infrared (FT-IR), ellipsometry, and X-ray photoelectron spectroscopy (XPS). The applicability of the catalytic polymer brushes in a microreactor was demonstrated for the Knoevenagel and nitroaldol condensation reactions, and the synthesis of coumarin derivatives. The catalytic activity of the microreactor was still intact even after 2 months.

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L‐Proline Catalyzed Solvent‐Free Knoevenagel Condensation for the Synthesis of 3‐Substituted Coumarins

Abstract: L-Proline was utilized as an efficient organo-catalyst for the environmentally benign synthesis of 3-substituted coumarins by the Knoevenagel condensation of substituted 2-hydroxybenzaldehydes with reactive methylene compounds under solvent free conditions.

Cited by 55 publications

References 35 publications

Synthesis, antioxidant and anticholinesterase activities of novel coumarylthiazole derivatives

Synthesis, antioxidant and anticholinesterase activities of novel coumarylthiazole derivatives

In vitro and in vivo trypanocidal activities of 8‐methoxy‐3‐(4‐nitrobenzoyl)‐6‐propyl‐2H‐cromen‐2‐one, a new synthetic coumarin of low cytotoxicity against mammalian cells

Piperazine-Containing Polymer Brush Layer as Supported Base Catalyst in a Glass Microreactor

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