An Efficient One-Pot Synthesis of Dihydropyrimidinones Under Solvent-Free Conditions

Hatamjafari, Farhad; Nezhad, Fatemeh Germani

doi:10.13005/ojc/300148

Cited by 9 publications

(7 citation statements)

References 28 publications

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“…The (DHPMs) have attracted great attention recently in synthetic organic chemistry due to their applications in the field of drug research and pharmacological and therapeutic properties such as antibacterial [3,4], anti-inflammatory [4], antiviral [5], antitumor [6], antimalarial agents [7], hypnotics, anticonvulsant, antithyroid, antihistaminic agents , antibiotics [2] and in addition, 4aryldihy-dropyrimidines have emerged antihypertensive activity as well as behaving as calcium channel blockers 8,9 ,α-antagonists and neuropeptide antagonists [10]. Synthesis of dihydropyrimidinone and their thio analogue is increasing tremendously in current years and also synthesized earlier a series of dihydropyrimidinone/thione by three component condensation of urea/thiourea [2].…”

Section: Introductionmentioning

confidence: 99%

Green Synthesis and Characterization of Dihydropyrimidinone Derivatives using Fruit Juice.

Kale¹

2019

JCPR

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A simple and precise green synthesis method that has been used to synthesis of dihydropyrimidinone (DHPMs) derivatives. The reaction involves three-component one-pot condensation of an aromatic aldehyde, β-ketoester and urea in lemon juice. A large number of Dihydropyrimidinone (DHPM) derivatives were synthesized using urea, ethyl acetoacetate with electron rich as well as electron deficient aromatic aldehydes. The different type of aldehyde used like benzaldehyde, 4-Chliorobenzaldehyde, 4-methoxybenzaldehyde, anisaldehyde, cinnamaldehyde, and salicyaldehyde etc. The fruit juice like orange, amla, lime juice without processing is used as catalyst. The recrystallized products obtained were identified using physical and spectroscopic techniques UV-Visible, IR, 1 HNMR etc. The yield of these reactions were found comparatively good and in the range of (80-95%). The advantage of this method is to initiate green chemistry approach in new researchers. The excellent yield, short time, operational simplicity, and the avoidance of the use of organic solvents and friendly preparation etc are the importance of the present work.

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Section: Introductionmentioning

confidence: 99%

Green Synthesis and Characterization of Dihydropyrimidinone Derivatives using Fruit Juice.

Kale¹

2019

JCPR

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“…Recently, several improved methodologies have been developed that use triethylbenzyl ammonium chloride 10 , p-dodecyl benzenesulfonic acid 11 , phosphomolybdic acid supported on silica gel 12 , sulfonic acid on silica gel 13 , HClO 4 -SiO 2 14 and ZnO 15 among others. Previously, we have synthesized a number of heterocyclic compounds [16][17][18][19][20][21][22][23][24][25][26] .…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of 1,8-Dioxo-octahydroxanthene Derivatives Using Zn(NO3)2 under Solvent-free Conditions

Vahabi¹,

Hatamjafari²,

Pourshamsian³

2014

Orient. J. Chem.

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“…Aromatic aldehydes, especially when used to replace for synthesis quinazolinones. Previously, we have synthesized a number of heterocyclic compounds [16][17][18][19][20][21][22][23][24][25][26][27][28] . Herein we report some of quinazolinones at one pot reaction, environmentally friendly with high yields and easy separation (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

An Efficient an One-Pot Method for Synthesis of 2-Aryl-(3H)-4-Quinazolinones Derivatives Catalyzed by SSA

Hatamjafari¹,

Eslami²

2014

Orient. J. Chem.

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A mixture of 2-amino benzamide with aromatic aldehyds in the presence of SSA under solvent-free condition were converted to quinazolinones with good yields.Key words: Starch SulphuricAcid (SSA), (3H)-4-Quinazolinones, One-pot, Solvent-Free . used in the synthesis of quinazolinone derivatives [6][7][8][9][10][11][12][13][14] .The early method, based on the reaction of 2-aminobenzamide with aldehyds, was performed in the presence of H 2 SO 4 and as a requirement of its refluxing condition much excess of aldehyds was used 15 .Though an excess of aldehyds is necessary to diminish the intermolecular side-reactions, the conventional beating method ever needs additional aldehyds both to improve the yield. In contrast to the Liquid H 2 SO 4, which is difficult to recovery and takes some effort in workup, the silica-supported H 2 SO 4, can be easily separated and recycled without the loss of activity for several times. Thus, 2-aminobenzamides (1) reacted with nearly 2 equivalents of aromatic aldehyds (2) 833-835 (2014) submission to microwave irradiation to provide fairly high yields of substituted quinazolin-4(3H)-ones (2a-d) in 25 minutes.However, these reactions often require harsh conditions and long reaction time and low efficiency can. Aromatic aldehydes, especially when used to replace for synthesis quinazolinones. Previously, we have synthesized a number of heterocyclic compounds [16][17][18][19][20][21][22][23][24][25][26][27][28] . Herein we report some of quinazolinones at one pot reaction, environmentally friendly with high yields and easy separation (Scheme 1). General Procedure for the Preparation of (3H)-4-Quinazolinone DerivativesA mixture of aldehyde (1 mmol) and2-amino benzamide (1 mmol), and starch sulphuric acid (20 W%) as a catalyst was stirred at 80 o C for 25 min. The progress of reaction was monitored by TLC. After finishing, recrystallized from ethanol 95% to give pure products (2a-d) 2-(3-nitrophenyl)-(3H)-4-Quinazolinone (2a)Pale 2-(4-methoxyphenyl)-(3H)-4-Quinazolinone (2b)Yellow crystals, Yield: %72, m.p= 245-248°C , FT-IR (V max /cm -1 ) (KBr disc): 3410 (amid NH Str.); 3131(arom. CH Str.); 2990(aliph. CH Str.); 1675(amid C=O Str.); 1643(C=N Str.). 2-(4-chlorophenyl)-(3H)-4-Quinazolinone (2c)White crystals, Yield: 89%, m.p = 302-304°C In conclusion, in comparison with the precedent related methods which show drawbacks from the standpoints of, prolong refluxing in solvent, need to inert gas, and consuming more aldehyds, the notable advantages of this methodology are: mild conditions in a solvent-free system, fairly high yields, fast reaction, no aqueous work-up and safe and environmental friendly conditions.

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An Efficient One-Pot Synthesis of Dihydropyrimidinones Under Solvent-Free Conditions

Abstract: An efficient method for one-pot synthesis of 3,4-Dihydropyrimidin-2-(1H) -one derivatives the Biginelli condensation reaction of aromaticaldehydes, b-ketoesters and urea under solvent-free conditions was described.

Cited by 9 publications

References 28 publications

Green Synthesis and Characterization of Dihydropyrimidinone Derivatives using Fruit Juice.

Green Synthesis and Characterization of Dihydropyrimidinone Derivatives using Fruit Juice.

One-Pot Synthesis of 1,8-Dioxo-octahydroxanthene Derivatives Using Zn(NO3)2 under Solvent-free Conditions

An Efficient an One-Pot Method for Synthesis of 2-Aryl-(3H)-4-Quinazolinones Derivatives Catalyzed by SSA

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