Ceric (IV) ammonium nitrate (CAN) mediated synthesis of pyrrole-2,3,4,5-tetracarboxylates by reaction of dimethyl acetylenedicarboxylate with an amine

Madabhushi, Sridhar; Vangipuram, Venkata Sairam; Mallu, Kishore Kumar Reddy; Jillella, Raveendra; Kurva, Srinivas; Pamulaparthi, Shanthan Rao

doi:10.1016/j.tetlet.2013.09.128

Cited by 14 publications

(5 citation statements)

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“…adamantylamine gave 73% yield). 66 In the absence of CAN, the only product observed was the 1 : 1 adduct of the amine to DMAD (Scheme 51). Almost simultaneously, Wu disclosed a very similar transformation promoted by copper acetate in an oxygen atmosphere.…”

Section: Multicomponent Pyrrole Syntheses From Alkynesmentioning

confidence: 99%

Recent advances in the synthesis of pyrroles by multicomponent reactions

2014

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Pyrrole is one of the most important one-ring heterocycles. The ready availability of suitably substituted and functionalized pyrrole derivatives is essential for the progress of many branches of science, including biology and materials science. Access to this key heterocycle by multicomponent routes is particularly attractive in terms of synthetic efficiency, and also from the environmental point of view. We update here our previous review on this topic by describing the progress made in this area in the period between mid-2009 and the end of 2013.

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Section: Multicomponent Pyrrole Syntheses From Alkynesmentioning

confidence: 99%

Recent advances in the synthesis of pyrroles by multicomponent reactions

2014

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“…The SET mechanism of CAN has also been reported by Madabhushi et al . . Low COD removal (30.9%) might be attributed to the presence of dye fragments (aliphatic/aromatic sulfonate derivatives) in decolorized solution, perhaps due to high resistance of these moieties towards Ce 4+ ion oxidation.…”

Section: Resultsmentioning

confidence: 99%

Elucidation of degradation mechanism of reactive blue 171 dye by ceric ammonium nitrate

Patil

Shukla

2016

Env Prog and Sustain Energy

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Oxidative degradation of azo chromophore based C. I. Reactive Blue 171 dye having recalcitrant triazine and naphthalene rings in the structure was attempted using ceric ammonium nitrate (CAN) as an oxidant. The extent of decolorization was evaluated, which was found to be maximum (93.1%) at pH 6.5 and CAN dosage 0.19 mM for 50 mg/L dye solution in 1 h. The COD removal was 30.9%. The kinetic study of dye degradation exhibited pseudo-firstorder kinetics. The effect of temperature was described by the Arrhenius equation and the activation energy was found to be 33.8 kJ/mol. The intermediates formed by the CAN treatment were analyzed by TLC, FTIR and HPLC, which indicated the breaking of bonds of the dye. GC/MS analysis indicated formation of smaller sulfonate fragments by azo bond cleavage. The degradation pathway for the dye pollutant has been predicted based on the characterization of the degradation products formed. Phytotoxicity, as analyzed by ANOVA, indicated results comparable with distilled water, revealing extensive reduction in toxicity of the dye upon CAN treatment. Thus, oxidative treatment with CAN gives effective decolorization, partial mineralization and extensive reduction in the toxicity of the dye RB 171, which allows safe reuse of the treated dye solution for irrigation purpose.

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“…It is interesting to note that isatinyl substituted products obtained using this method are unusual because under normal circumstances the reaction of isatin and 3-isatinylidene compounds usually provides spirocyclic oxindoles. 102 Madabhushi and co-workers 103 reported a facile approach for the preparation of fully functionalized pyrrole derivatives 43 from amine 41 and dimethyl acetylenedicarboxylate 42 using ceric(IV) ammonium nitrate (Scheme 9). The cyclocondensation of two units of DMAD and one unit of primary amine resulted in the formation of a symmetrical pentasubstituted pyrrole.…”

Section: Aliya Ibrarmentioning

confidence: 99%