Hypophosphite Addition to Alkenes Under Solvent-Free and Non-Acidic Aqueous Conditions

Aim and Objective: In this work, we synthesized and characterized a novel Brönsted acidic ionic liquid from the reaction of N, N, N’, N’-tetramethylethylenediamine with chlorosulfonic acid and explored its catalytic activity in 1, 8-dioxo-octahydroxanthenes synthesis. Materials and Methods: Dimedone, aryl aldehydes, and the ionic liquid as the catalyst were reacted under solvent-free conditions. The progressive of the reaction was monitored by a thin layer of chromatography (ethyl acetate/n-hexane = 1/5). All products were characterized as the basis of their spectra data and melting point by comparison with those reported in the literature. Results: The prepared ionic liquid was successfully applied in the synthesis of 1, 8-dioxooctahydroxanthenes in good to high yields on the reaction of aryl aldehyde and dimedone at 120oC under solvent-free conditions. Conclusion: This research demonstrates that the catalyst is impressive for 1, 8-dioxo-octahydroxanthenes synthesis under solvent-free conditions.

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A highly efficient and green approach for the synthesis of pyrimido[4,5-b]quinolines using N,N-diethyl-N-sulfoethanaminium chloride

Zeitschrift für Naturforschung B ◽

10.1515/znb-2020-0098 ◽

2021 ◽

Vol 76 (2) ◽

pp. 85-90

Author(s):

Abdolkarim Zare ◽

Manije Dianat

Keyword(s):

Reaction Times ◽

Solvent Free ◽

One Pot ◽

Catalyst Amount ◽

Green Protocol ◽

Highly Efficient ◽

Green Approach ◽

Solvent Free Conditions ◽

The One ◽

High Yields

Abstract A highly efficient and green protocol for the synthesis of pyrimido[4,5-b]quinolines has been described. The one-pot multicomponent reaction of dimedone with arylaldehydes and 6-amino-1,3-dimethyluracil in the presence of N,N-diethyl-N-sulfoethanaminium chloride ([Et3N–SO3H][Cl]) as an ionic liquid (IL) catalyst under solvent-free conditions afforded the mentioned compounds in high yields and short reaction times. Our protocol is superior to many of the reported protocols in terms of two or more of these factors: the reaction times, yields, conditions (solvent-free versus usage of organic solvents), temperature and catalyst amount.

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Solid-state regioselective nitration of activated hydroxyaromatics and hydroxycoumarins with cerium (IV) ammonium nitrate

Journal of Chemical Research ◽

10.3184/030823405774909342 ◽

2005 ◽

Vol 2005 (11) ◽

pp. 733-735 ◽

Cited By ~ 4

Author(s):

Nemai C. Ganguly ◽

Sanjoy Dutta ◽

Mrityunjoy Datta ◽

Prithwiraj De

Keyword(s):

Solid State ◽

Ammonium Nitrate ◽

High Efficiency ◽

Solvent Free ◽

High Melting ◽

Microwave Assisted ◽

Solvent Free Conditions ◽

High Yields ◽

Regioselective Nitration ◽

Cerium Iv Ammonium Nitrate

Predominant ortho-selective mononitration of low-melting and liquid phenols and hydroxycoumarins in moderate to high yields has been accomplished upon grinding with solid cerium (IV) ammonium nitrate (CAN). Microwave-assisted expeditious CAN-mediated nitration of relatively high melting phenols and hydroxycoumarins with high efficiency and selectively under solvent-free conditions has been also developed to address the problems of sluggishness and low yield for these reluctant substrates.

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Rapid and Green One-Pot Synthesis of Novel 2-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-diones

Letters in Organic Chemistry ◽

10.2174/1570178618666210615101248 ◽

2021 ◽

Vol 18 ◽

Author(s):

Abolfazl Olyaei ◽

Zahra Ghahremany ◽

Madieh Sadeghpour

Keyword(s):

Aromatic Amines ◽

Low Cost ◽

Guanidine Hydrochloride ◽

Reaction Times ◽

Solvent Free ◽

One Pot ◽

Solvent Free Conditions ◽

The One ◽

High Yields ◽

Work Up

: A green and efficient protocol was developed for the one-pot three-component synthesis of novel 2-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-dione derivatives by the reaction of 4-hydroxycoumarin, ninhydrin and aromatic amines in the presence of guanidine hydrochloride as an organocatalyst under solvent-free conditions. The present approach offers several advantages such as low cost, simple work-up, short reaction times, chromatography-free purification, high yields and greener conditions.

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Solid lithium perchlorate as a powerful catalyst for the synthesis of β-aminoalcohols under solvent-free conditions

Canadian Journal of Chemistry ◽

10.1139/v05-062 ◽

2005 ◽

Vol 83 (5) ◽

pp. 505-507 ◽

Cited By ~ 10

Author(s):

Najmodin Azizi ◽

Mohammad R Saidi

Keyword(s):

Ring Opening ◽

Room Temperature ◽

Lithium Perchlorate ◽

Solvent Free ◽

Solvent Free Conditions ◽

Reaction Proceeds ◽

Ring Opening Of Epoxides ◽

Neutral Conditions ◽

Hindered Amines ◽

Short Times

Lithium perchlorate catalyzed the ring opening of epoxides with amines to provide the corresponding β-aminoalcohols in excellent yields with high regioselectivity. The reaction proceeds rapidly under mild and neutral conditions and worked well with primary, secondary, aliphatic, aromatic, and hindered amines in short times at room temperature, in the absence of solvent.Key words: epoxide, lithium perchlorate, β-aminoalcohols, solvent-free.

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Conversion of hydroxyl groups into bromo groups in carbohydrates with inversion of configuration

Canadian Journal of Chemistry ◽

10.1139/v81-053 ◽

1981 ◽

Vol 59 (2) ◽

pp. 339-343 ◽

Cited By ~ 53

Author(s):

Björn Classon ◽

Per J. Garegg ◽

Bertil Samuelsson

Keyword(s):

Elevated Temperature ◽

Hydroxyl Groups ◽

Secondary Hydroxyl ◽

Reaction Proceeds ◽

One Step ◽

High Yields

A novel reagent system is described for the efficient, one-step transformation of hydroxyl groups in carbohydrates to bromodeoxy groups. The reaction proceeds with inversion of configuration. The reagent system consists of triphenylphosphine, tribromoimidazole, and imidazole in toluene at elevated temperature. The carbohydrate need not be soluble in toluene. The examples given include substitution of isolated primary and secondary hydroxyl groups in otherwise protected carbohydrates as well as disubstitution involving one primary and one secondary position in hexopyranosides. High yields are obtained in the replacement of hydroxyl by bromine in the 2-position of 3,4,6-protected methyl α-D-gluco- and -mannopyranosides.

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TiO2–SiO2 nanocomposite as a highly efficient catalyst for the solvent-free cyclocondensation reaction of isatins, cyclohexanones, and urea

Zeitschrift für Naturforschung B ◽

10.1515/znb-2019-0059 ◽

2019 ◽

Vol 74 (7-8) ◽

pp. 559-564

Author(s):

Simin Janitabar-Darzi ◽

Shahrzad Abdolmohammadi

Keyword(s):

Present Method ◽

High Efficiency ◽

Solvent Free ◽

High Catalytic Activity ◽

One Pot ◽

Efficient Catalyst ◽

Solvent Free Conditions ◽

Cyclocondensation Reaction ◽

The One ◽

High Yields

AbstractA TiO2–SiO2 nanocomposite catalyzes the one-pot cyclocondensation reaction of 1H-indole-2,3-diones (isatins), 1,3-cyclohexanediones, and urea at T = 70°C under solvent-free conditions with high efficiency. The present method affords the corresponding spiro products in high yields and short reaction time. The unique features of the TiO2–SiO2 nanocomposite are high catalytic activity, ease of preparation, non-toxicity, low loading, and recyclability.

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A One-Pot, Three-Component, Solvent-Free Synthesis of Novel 6H-Chromeno[3’,4’:5,6]Pyrido[2,3-d]Pyrimidine-Triones under Microwave Irradiation

Journal of Chemical Research ◽

10.3184/174751918x15414289771620 ◽

2018 ◽

Vol 42 (12) ◽

pp. 604-607

Author(s):

Loghman Firoozpour ◽

Hoda Yahyavi ◽

Ramona Ejtemaei ◽

Setareh Moghimi ◽

Alireza Foroumadi

Keyword(s):

Microwave Irradiation ◽

Efficient Method ◽

Barbituric Acid ◽

Reaction Times ◽

Solvent Free ◽

One Pot ◽

Solvent Free Conditions ◽

Substituted Benzaldehydes ◽

High Yields ◽

Solvent Free Synthesis

A green and efficient method for preparing novel heterocyclic systems is established through the reaction of differently substituted benzaldehydes, barbituric acid and 4-amino-2H-chromene-2-one under solvent-free conditions. This method affords 6H-chromeno[3’,4’:5,6] pyrido[2,3-d]pyrimidine-trione derivatives in high yields and short reaction times.

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Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD®/Olah’s reagent under solvent-free conditions

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.16.254 ◽

2020 ◽

Vol 16 ◽

pp. 3052-3058

Author(s):

Yumeng Liang ◽

Akihito Taya ◽

Zhengyu Zhao ◽

Norimichi Saito ◽

Norio Shibata

Keyword(s):

Reaction Mechanism ◽

Solvent Free ◽

Reaction Conditions ◽

Great Tolerance ◽

Solvent Free Conditions ◽

Synthetic Drug ◽

High Yields

A new protocol enabling the formation of trifluoromethyl compounds from acyl fluorides has been developed. The combination of FLUOLEAD® and Olah’s reagent in solvent-free conditions at 70 °C initiated the significant deoxyfluorination of the acyl fluorides and resulted in the corresponding trifluoromethyl products with high yields (up to 99%). This strategy showed a great tolerance for various acyl fluorides containing aryloyl, (heteroaryl)oyl, or aliphatic acyl moieties, providing good to excellent yields of the trifluoromethyl products. Synthetic drug-like molecules were also transformed into the corresponding trifluoromethyl compounds under the same reaction conditions. A reaction mechanism is proposed.

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Synthesis of β-amino alcohols using MgO as a new catalyst under solvent-free conditions

Canadian Journal of Chemistry ◽

10.1139/v07-135 ◽

2008 ◽

Vol 86 (1) ◽

pp. 65-71 ◽

Cited By ~ 7

Author(s):

Mona Hosseini-Sarvari

Keyword(s):

Ring Opening ◽

Amino Alcohols ◽

Solvent Free ◽

Aliphatic Amines ◽

Solvent Free Conditions ◽

Ring Opening Of Epoxides ◽

High Yields ◽

Aromatic And Aliphatic Amines

MgO catalyzed efficiently the ring opening of epoxides with a range of aromatic and aliphatic amines to produce β-substituted alcohols in high yields under solvent-free conditions. Exclusive trans stereoselectivity is observed for cyclic epoxide.Key words: MgO, β-amino alcohols, solvent-free, epoxide, amine.

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