A new protocol for Biginelli (or like) reaction under solvent-free grinding method using Fe (NO3)3.9H2O as catalyst

Phukan, Mridula; Kalita, Monoj Mon; Borah, Ruli

doi:10.1080/17518253.2010.487841

Cited by 37 publications

(14 citation statements)

References 31 publications

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“…In continuation [15][16][17] of our development of environmentally benign syntheses, we examined the catalytic activity of supported acids (PANI-TsOH, PANI-FeCl 3 , Clayfen) and conventional Brønsted or Lewis acid (TsOH, FeCl 3 , Fe(NO 3 ) 3 .9H 2 O) catalysts in the synthesis of xanthenedione derivatives from aromatic aldehydes and 5,5-dimethyl-1,3-cyclohexanedione in solution under reflux and solventfree grinding condition at ambient temperature. In this context, to study the activity of various catalysts in solution and solvent-free grinding conditions we selected the reactions of pchlorobenzaldehyde (1 mmol) and 5,5-dimethyl-1,3-cyclohexanedione (2 mmol) which led to xanthenedione derivative 4.…”

Section: Resultsmentioning

confidence: 99%

Investigation of efficient synthesis of 1, 8-dioxo-octahydroxanthene derivatives under solvent-free grinding method

Borah¹,

Dutta²,

Sarma³

2013

10.5267/j.ccl

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In these studies, we had observed polyaniline (PANI) supported p-toluene sulfonic acid (TsOH) and FeCl 3 (PANI-TsOH, PANI-FeCl 3 ) as excellent reusable solid acid catalysts for the synthesis of 1, 8-dioxo-octahydroxanthene derivatives 4(a-g) under solvent-free grinding method at mild conditions. Additionally, in the same optimized condition ferric nitrate nonahydrate also acted as (non-reusable) very reactive inexpensive Lewis acid catalyst. The ferric nitrate nonahydrate lost its activity in the form of Clayfen (Clay-supported ferric nitrate) catalyst.

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Section: Resultsmentioning

confidence: 99%

Investigation of efficient synthesis of 1, 8-dioxo-octahydroxanthene derivatives under solvent-free grinding method

Borah¹,

Dutta²,

Sarma³

2013

10.5267/j.ccl

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“…The results show the position and the property of the substituents on the aromatic ring do not show effects on the conversion. Under the solvent-free conditions, the yields and reaction time were significantly better than the reported procedures (7)(8)(9)(10)(11)(12)(13)(14)(15)(16). A possible mechanism for this transformation is proposed (Scheme 2) (18).…”

mentioning

confidence: 85%

One-pot Synthesis of 5-Unsubstituted 3,4-Dihydropyrimidin-2(1H)-ones from Aldehydes, Ketones, and Urea under Solvent-free Conditions

Song

Sun

Yang

2015

Polycyclic Aromatic Compounds

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Various 5-unsubstituted 3,4-dihydropyrimidin-2(1H)-ones were synthesized efficiently by a one-pot three-component condensation of aromatic aldehydes, aromatic ketones, and urea using SnCl 2 ·2H 2 O as a catalyst under solvent-free conditions. All products were identified by IR, NMR, MS, and elemental analysis. The novel method offers several advantages such as excellent yields (81-95%), short reaction time (5-16 min), broader substrate scope, and environmentally friendly conditions.

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“…Dihydropyrimidin‐2(1H)‐ones/thiones displayed variety of biological activity [5–7] . Hence, several homogeneous catalysts especially Lewis acids such as BiCl 3 , Bi(OTf) 3 , Bi(NO 3 ) 3 , CeCl 3 7H 2 O, Cu(OTf) 2 , CuCl 2 2H 2 O/CuSO 4 5H 2 O, Fe(NO 3 ) 3 9H 2 O, Fe(OTs) 3 6H 2 O, GaCl 3 , Hf(OTf) 4, In(OTf) 3 , RuCl 3 , SbCl 3 , SnCl 2 2H 2 O, Sr(OTf) 2 , TiCl 4 , Yb(OTf) 3 , ZnCl 2 , ZrCl 4 and ZrCl 4 or ZrOCl 2 8H 2 O [8–27] subsequently were developed to enhance the yield of product. All mentioned catalysts improved the yield of product but most of them are expensive; difficult to remove from solution consequently metal traces can be remained in the final product and reusability are the key issues.…”

Section: Introductionmentioning

confidence: 99%

Fe(III)/Bentonite as a Heterogeneous Catalyst for the Synthesis of 3,4‐dihydropyrimidin‐2‐(1H)‐ones

Chopda

Dave

2020

ChemistrySelect

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Fe(III) immobilized over natural bentonite (bent) using the impregnation method. Prepared catalysts were well characterized by XRD, FT-IR and FeSEM. The catalytic activity of three catalysts 10, 20 and 30 % Fe(III)/bent evaluated for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones known as Biginelli reaction. The catalyst 30 % Fe(III)/bent exhibited a high yield of the product towards the synthesis of a variety of dihydropyrimidones (DHPMs). The high yield of dihydropyrimidone (DHPM) was obtained in model reaction in ethanol, acetonitrile, DMF and solvent-free condition. The reusability test indicated that 6 % of yield of product decreased after 5 th cycle. Highlights * 10, 20 and 30 % Fe(III) were supported over bentonite clay. The catalysts are well characterized by (XRD), FT-IR, FeSEM and EDS. All charactization method showed that Fe supported over bentonite. * The used catalysts were screened for Biginelli reaction for synthesis dihydropyrimidones. * 30 % Fe(III)/bent exhibited high yield of product towards model Biginelli reaction between benzaldehyde, ethylacetoacetate and urea in ethanol. * 30 % Fe(III)/bent exhibited high yield of product in CH 3 CN, DMF and solvent free-condition. * The catalyst 30 % Fe(III)/bent applied for synthesis of variety of dihydropyrimodone in good yield in CH 3 CN. * Reusability studies show that no great decline in activity after 5 th cycle.

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A new protocol for Biginelli (or like) reaction under solvent-free grinding method using Fe (NO₃)₃.9H₂O as catalyst

Cited by 37 publications

References 31 publications

Investigation of efficient synthesis of 1, 8-dioxo-octahydroxanthene derivatives under solvent-free grinding method

Investigation of efficient synthesis of 1, 8-dioxo-octahydroxanthene derivatives under solvent-free grinding method

One-pot Synthesis of 5-Unsubstituted 3,4-Dihydropyrimidin-2(1H)-ones from Aldehydes, Ketones, and Urea under Solvent-free Conditions

Fe(III)/Bentonite as a Heterogeneous Catalyst for the Synthesis of 3,4‐dihydropyrimidin‐2‐(1H)‐ones

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