A benign synthesis of 2-amino-4H-chromene in aqueous medium using hydrotalcite (HT) as a heterogeneous base catalyst

Kale, Sandip R.; Kahandal, Sandeep S.; Burange, Anand S.; Gawande, Manoj B.; Jayaram, Radha V.

doi:10.1039/c3cy20856g

Cited by 83 publications

(27 citation statements)

References 52 publications

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“…Several synthetic methods have been widely applied for synthesis of pyran-based heterocyclic compounds, using many homogeneous or heterogeneous organic, inorganic, and nanomaterial catalysts, for example hexamethylenetetramine (HMT) [40], heteropolyacid [41], diammonium hydrogen phosphate [42], DBU [43], piperidine [44][45][46][47], tetrabutylammonium bromide (TBAB) [48], ionic liquids [49], morpholine [50], 4-(dimethylamino)pyridine (DMAP) [51], urea [52], 3-hydroxypropanaminium acetate (HPAA) [53], N-propylpiperazine sodium n-propionate (SBPPSP) [54], silica gel [55], sulfonic acid-functionalized silica [ [60], meglumine [61], I 2 /K 2 CO 3 [62], cetyltrimethylammonium bromide (CTABr) [63], nano-sized MgO [64], nano-structured Na 2 CaP 2 O 7 [65], NaHCO 3 [66], Na 2 CO 3 [67], triazine-functionalized ordered mesoporous organosilica [68], potassium phosphate tribasic trihydrate [69], Mg/Al hydrotalcite [70], Amberlyst A21 [71], DABCO [72], CeO 2 /CaO nanocomposite oxide [73], triton B [74], tetrabutylammonium chloride (TBAC) [75], nano-eggshell powder [76], basic alumina [77], [bmim]OH [78,79], LiBr [80], glycine [81], silica nanoparticles [82], ionic liquid choline chlorid...…”

Section: Introductionmentioning

confidence: 99%

Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

Kiyani

Ghorbani

2014

Res Chem Intermed

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A variety of 4H-chromenes, benzochromenes, 4,5-dihydropyrano[3,2-c]chromenes, 4H-pyran-3-carboxylates, and 3,4-disubstituted isoxazol-5(4H)-ones have been synthesized in high yields by using potassium hydrogen phthalate (KHP) as an inexpensive, commercially available catalyst. It was found that the threecomponent tandem reaction enabled synthesis of pyran-annulated heterocycles in water at 50°C. 3,4-Disubstituted isoxazol-5(4H)-ones were synthesized by use of 10 mol% KHP in water at room temperature. Also, treatment of methylene-containing compounds (malononitrile or ethyl cyanoacetate) with aromatic aldehydes in the presence of 5 mol% KHP resulted in a,b-unsaturated nitriles. The procedure is an easily performed, straightforward method for synthesis of a variety of pyranannulated compounds, isoxazol-5(4H)-one-containing heterocycles, and Knoevenagel adducts. The reaction is safe, uses mild conditions, and is environmentally benign. Other notable advantages are reuse of the catalyst, no use of hazardous organic solvents, and ease of work-up.

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Section: Introductionmentioning

confidence: 99%

Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

Kiyani

Ghorbani

2014

Res Chem Intermed

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“…In continuation of our efforts for synthesis of organic compounds using sustainable protocols (Gawande et al, 2013a,b,c,d, 2014a,b,c; Kale et al, 2013; Sharma et al, 2015), in this work, we have successfully developed a mild and ecofriendly synthesis of benzyl phosphonates using PEG/KI as a catalytic system. In this protocol, PEG not only acts as a reaction medium but also as a PTC.…”

Section: Resultsmentioning

confidence: 96%

A Sustainable and Efficient Synthesis of Benzyl Phosphonates Using PEG/KI Catalytic System

et al. 2016

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An efficient and expedient protocol for the synthesis of benzyl phosphonates using KI/K2CO3 as a catalytic system and PEG-400 as benign solvent has been developed. The reaction proceeds smoothly at room temperature achieving excellent selectivity and yield of the corresponding products. The combination of PEG-400, KI, and K2CO3 in this reaction avoids the need of volatile/toxic organic solvents and reactive alkali metals or metal nanoparticles/hydrides. We believe that this benign combination (PEG-400 and KI) could be used for other related organic transformations.

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“…According to the literature [48,49], 2-benzylidenemalononitrile, containing the electron-poor C_C double bond, is formed by Knoevenagel addition of malononitrile to benzaldehyde in the presence neutral ionic liquid OAc as catalyst. Then, 2-benzylidenemalononitrile has been attacked by resorcinol in the presence of neutral ionic liquid OAc, which leads to the 2-amino-7-hydroxy-4-phenyl-4H-chromene-3-carbonitrile.…”

Section: Determination Of Model Adequacymentioning

confidence: 99%

Preparation of neutral ionic liquid [2-Eim] OAc with dual catalytic-solvent system roles for the synthesis of 2-amino-3-cyano-7-hydroxy-4-(aryl)-4H-chromene derivatives

Ghorbani

Noura

Oftadeh

et al. 2015

Journal of Molecular Liquids

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A benign synthesis of 2-amino-4H-chromene in aqueous medium using hydrotalcite (HT) as a heterogeneous base catalyst

Cited by 83 publications

References 52 publications

Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

A Sustainable and Efficient Synthesis of Benzyl Phosphonates Using PEG/KI Catalytic System

Preparation of neutral ionic liquid [2-Eim] OAc with dual catalytic-solvent system roles for the synthesis of 2-amino-3-cyano-7-hydroxy-4-(aryl)-4H-chromene derivatives

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