Novel procedure for the synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using polymer-supported Burgess reagent under microwave conditions

Brain, Christopher T.; Paul, Jane M.; Loong, Yvonne; Oakley, Paul

doi:10.1016/s0040-4039(99)00382-2

Cited by 177 publications

(58 citation statements)

References 18 publications

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“…They are considered as . [5] or under microwave irradiation of N,N′-diacylhydrazines by grafting onto polymer support [6][7][8]. Hydrazides are considered to be an important class of compounds with various types of biological activity such as anti-bacterial [9], anti-in ammatory, anti-cancer [10], anti-microbial [11,12], anti-fungal [9,13] and anti-biotic [13][14][15].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of N′-(2-phenylacetyl)thiophene-2-carbohydrazide monohydrate, C₁₃H₁₄N₂O₃S

El‐Faham

El-Merghany

Ghabbour

2016

Zeitschrift Für Kristallographie - New Crystal Structures

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CCDC no.: 1479028The crystal structure is shown in the gure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters. Source of materialThiophene-2-carbonyl chloride (1.6 g, 11 mmol) in 10 mL dichloromethane was added dropwise to a mixture of hydrazide (1.50 g, 10 mmol) and NaOH (0.4 g, 10 mmol) in 30 mL dichloromethane and 20 mL water at 0°C. After complete addition of acid chloride, the reaction mixture was continued stirring at 0°C for 2 hours and at room temperature another 2 hours. The organic layer was separated and the aqueous layer extracted with another 50 mL dichloromethane. The collected organic layer was washed with water (20 mL), saturated NaCl solution (20 mL), and then dried over anhydrous MgSO4. The dichloromethane was ltered from MgSO4 and then was concentered under reduced pressure to give a white solid. The crude product was recrystallized from ethanol to a ord the pure product in 85% yield. (mp 220-1°C Experimental detailsCarbon-bound hydrogen atoms were placed in calculated positions and were included in the re nement in the riding model approximation, with U iso (H) set to 1.2Ueq(C). DiscussionBishydrazides (N,N′-diacylhydrazines) are usually obtained from esters, acid chlorides or acids [1]. They are considered as

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Section: Discussionmentioning

confidence: 99%

Crystal structure of N′-(2-phenylacetyl)thiophene-2-carbohydrazide monohydrate, C₁₃H₁₄N₂O₃S

El‐Faham

El-Merghany

Ghabbour

2016

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Examples of resin-bound reactions: synthesis of 1,3,4-oxadiazoles using Burgess reagent, [249] Wittig reactions with triarylphosphanes, [250] catalytic transfer reaction involving formate, [251] O-alkylation with O-alkyl isoureas, [252] and formation of amide bonds with carbodiimide. [253] HOBt = 1-hydroxybenzotriazole.…”

Section: Microwave Chemistrymentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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Although fire is now rarely used in synthetic chemistry, it was not until Robert Bunsen invented the burner in 1855 that the energy from this heat source could be applied to a reaction vessel in a focused manner. The Bunsen burner was later superseded by the isomantle, oil bath, or hot plate as a source for applying heat to a chemical reaction. In the past few years, heating and driving chemical reactions by microwave energy has been an increasingly popular theme in the scientific community. This nonclassical heating technique is slowly moving from a laboratory curiosity to an established technique that is heavily used in both academia and industry. The efficiency of “microwave flash heating” in dramatically reducing reaction times (from days and hours to minutes and seconds) is just one of the many advantages. This Review highlights recent applications of controlled microwave heating in modern organic synthesis, and discusses some of the underlying phenomena and issues involved.

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“…synthesis of 1,3,4-oxadiazoles, especially from available carboxylic acids and acid hydrazides. [14][15][16] As part of our ongoing program to develop efficient and robust methods for the synthesis of heterocyclic compounds, 17-20 we wish to report the preparation of a new class of 1,3,4-oxadiazole derivatives 5a-o by a novel Four-component condensation reaction of chloroacetone 1, primary amine 2, (N-isocyanimino)triphenylphosphorane 4 and (E)-cinnamic acids 3 in excellent yields under neutral conditions (Scheme 1).…”

Section: 10mentioning

confidence: 99%

Preparation of Fully Substituted 1,3,4-Oxadiazole Derivatives from N-Isocyaniminotriphenylphosphorane, (E)-Cinnamic Acids, Chloroacetone and Primary Amines

Ramazani¹,

Nasrabadi²,

Karimi³

et al. 2011

Bulletin of the Korean Chemical Society

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The 1:1 imine intermediate generated by the addition of primary amine to chloroacetone is trapped by Nisocyaniminotriphenylphosphorane in the presence of (E)-cinnamic acids and the corresponding iminophosphorane intermediate was formed. Disubstituted 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were completed in neutral conditions at room temperature. The disubstituted 1,3,4-oxadiazole derivatives were produced in excellent yields.

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Novel procedure for the synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using polymer-supported Burgess reagent under microwave conditions

Cited by 177 publications

References 18 publications

Crystal structure of N′-(2-phenylacetyl)thiophene-2-carbohydrazide monohydrate, C₁₃H₁₄N₂O₃S

Crystal structure of N′-(2-phenylacetyl)thiophene-2-carbohydrazide monohydrate, C₁₃H₁₄N₂O₃S

Controlled Microwave Heating in Modern Organic Synthesis

Preparation of Fully Substituted 1,3,4-Oxadiazole Derivatives from N-Isocyaniminotriphenylphosphorane, (E)-Cinnamic Acids, Chloroacetone and Primary Amines

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Novel procedure for the synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using polymer-supported Burgess reagent under microwave conditions

Cited by 177 publications

References 18 publications

Crystal structure of N′-(2-phenylacetyl)thiophene-2-carbohydrazide monohydrate, C13H14N2O3S

Crystal structure of N′-(2-phenylacetyl)thiophene-2-carbohydrazide monohydrate, C13H14N2O3S

Controlled Microwave Heating in Modern Organic Synthesis

Preparation of Fully Substituted 1,3,4-Oxadiazole Derivatives from N-Isocyaniminotriphenylphosphorane, (E)-Cinnamic Acids, Chloroacetone and Primary Amines

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Crystal structure of N′-(2-phenylacetyl)thiophene-2-carbohydrazide monohydrate, C₁₃H₁₄N₂O₃S

Crystal structure of N′-(2-phenylacetyl)thiophene-2-carbohydrazide monohydrate, C₁₃H₁₄N₂O₃S