Catalyst‐Free Strecker Reaction in Water: A Simple and Efficient Protocol Using Acetone Cyanohydrin as Cyanide Source

Galletti, Paola; Pori, Matteo; Giacomini, Daria

doi:10.1002/ejoc.201100089

Cited by 41 publications

(30 citation statements)

References 48 publications

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“…However, none of them proceeded without the use of catalyst. The current trend towards development of catalystfree [27][28][29] and solvent-free 30-32 reaction conditions encouraged us to study the same reaction without the use any catalyst or solvent. The remarkable success obtained in this investigation is presented herein.…”

Section: One-pot Synthesis Of 23-dihydroquinazolin-4(1h)-ones Under mentioning

confidence: 99%

One-pot Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones under Catalyst- and Solvent-free Conditions

Gupta

Samanta

Mallik

2015

Organic Preparations and Procedures International

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Small heterocyclic rings constitute one of the richest sources of diversity for medicinal chemists and more than half of biologically active molecules belong to various categories of quinazolinones. 1 Among them, 2,3-dihydro-4(1H)-quinazolinones remain a major source for the design of therapeutic drugs. 2 Moreover, they are building blocks for more than 150 naturally occurring pharmacologically active alkaloids and commercial drugs. 3,4 Their pharmaceutical character include anti-malarial, 5 anti-bacterial, 6 anti-tumor, 7 anticancer, 8 anti-fungal, 8 anti-convulsant 9 and monoamine oxidase inhibitory activities. 10 There are a number of methods for preparation of this class of compounds, the most direct one involving the condensation of aryl, alkyl, and heteroaryl aldehydes with anthranilamide in the presence of catalysts and solvents such as NH 4 Cl, 11 NaHSO 4 , 12 b-cyclodextrin, 13 cellulose-SO 3 H, 14 Amberlyst 15, 15 [PYC 4 SO 3 H][HSO 4 ]/A300SiO 2 , 16 Sc(OTf) 3 , 17 heteropoly acids, 18 cyanuric chloride, 19 transition metal-carbon nanotube (M-CNT) nanocomposites, 20,21 2-morpholinoethanesulfonic acid, 22 propylphosphonic anhydride (T3P Ò ), 23 K 3 PO 4 .H 2 O, 24 p-sulfonic acid calix[4]arene 25 or trifluoroethanol. 26 All of these reactions are successful in producing the target compound although certain drawbacks, such as use of harmful solvents, expensive catalysts, and low yields, are associated with some of them. With the goal of making some of the above-mentioned methods benign, the reactions were carried out under solvent-free conditions 16,20,21 , using MW-irradiation 21,22 and of water 18,22,24,25 or ethanol 11,12,17,22 as solvents. However, none of them proceeded without the use of catalyst. The current trend towards development of catalystfree 27-29 and solvent-free 30-32 reaction conditions encouraged us to study the same reaction without the use any catalyst or solvent. The remarkable success obtained in this investigation is presented herein.Our present methods involve subjecting an intimate mixture of anthranilamide and aldehyde/ketone (1:1 mole ratio) directly to heat (120 C, 10 min) or microwave (300 W, 3 min) irradiation. The time and temperature for the thermal reaction and the time and power for the MWI process were then optimized ( Table 1). A range of structurally diverse aryl and heteroaryl aldehydes and two cyclic ketones were examined and gave the target compounds 3 (Scheme 1) in yields greater than 90% ( Table 2).In the methods reported, it was a common observation that the reactions were very clean, and no side-products were formed in any run. In fact, the crude products obtained were of high purity and did not require any chromatographic separation; crystallization

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Section: One-pot Synthesis Of 23-dihydroquinazolin-4(1h)-ones Under mentioning

confidence: 99%

One-pot Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones under Catalyst- and Solvent-free Conditions

Gupta

Samanta

Mallik

2015

Organic Preparations and Procedures International

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“…Organic reactions under solvent-free and catalyst-free [18][19][20][21][22][23] conditions have increasingly attracted interest of chemists, particularly from the viewpoint of green chemistry. Though a number of solvent-free methodologies are known for effecting Knoevenagel condensation 13,15,16,24 , only a few catalyst-free reaction conditions are reported 25,26 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a Series of 2-Indolylmethylene-Linked Compounds by Thermal Knoevenagel Condensation Under Catalyst- And Solvent-Free Conditions

Halder

Sepay²,

Mallik³

2017

ECB

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“…In general, a-aminonitriles are synthesized by the reactions of aldehydes/ketones with amines in the presence of a cyanide source such as HCN [10,11], KCN [12], TMSCN [13,14], (EtO) 2 P(O)CN [15], Et 2 AlCN [16], Bu 3 SnCN [17,18], MeCOCN [19], acetone cyanohydrin [20,21] and ethyl cyanoformate [22,23]. However, these cyanide sources are often hazardous and toxic, and involve harsh reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Eco-friendly synthesis of α-aminonitriles from ketones in PEG-400 medium using potassium Hexacyanoferrate(II) as cyanide source

2012

Journal of Organometallic Chemistry

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Catalyst‐Free Strecker Reaction in Water: A Simple and Efficient Protocol Using Acetone Cyanohydrin as Cyanide Source

Cited by 41 publications

References 48 publications

One-pot Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones under Catalyst- and Solvent-free Conditions

One-pot Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones under Catalyst- and Solvent-free Conditions

Synthesis of a Series of 2-Indolylmethylene-Linked Compounds by Thermal Knoevenagel Condensation Under Catalyst- And Solvent-Free Conditions

Eco-friendly synthesis of α-aminonitriles from ketones in PEG-400 medium using potassium Hexacyanoferrate(II) as cyanide source

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