Water as a Green Solvent for Fast and Efficient Reduction of Carbonyl Compounds with NaBH<sub>4</sub>under Microwave Irradiation

Zeynizadeh, Behzad; Setamdideh, Davood

doi:10.1002/jccs.200500169

Cited by 26 publications

(15 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…To prevent the retro aza-Michael reaction in the aliphatic addition series, in situ reduction of the addition products was necessary and we envisaged that this entire process could be carried out in water. Thus, LGO was stirred with a series of aliphatic amines in water and when the consumption of LGO was complete ( 1 H NMR), two equivalents of NaBH 4 was added [32] (Scheme 3). In this two-step one-pot process, the aza-Michael reaction was completely exo-selective, however, the reduction step (which usually proceeds via exo approach [33] ) proceeded with varying levels of diastereoselectivity.…”

Section: Resultsmentioning

confidence: 99%

“…2-Bromoaniline gave the aza-Michael product 2b in much better yield than the literature procedure outlined in Scheme 1. Thus, LGO was stirred with a series of aliphatic amines in water and when the consumption of LGO was complete ( 1 H NMR), two equivalents of NaBH 4 was added [32] (Scheme 3). The 4-cyano and 2-methoxycarbonylanilines afforded the addition products 2g and 2h in good yield, demonstrating that mildly electron-poor substituents were tolerated.…”

Section: Aza-michael Additions Tomentioning

confidence: 99%

See 1 more Smart Citation

Bio‐Based Chiral Amines via Aza‐Michael Additions to (–)‐Levoglucosenone Under Aqueous Conditions

et al. 2018

View full text Add to dashboard Cite

Chiral amines are highly coveted within the fine‐chemical industry and sustainable synthetic methodologies for their production are of great value. By harnessing the chirality present in cellulose‐derived (–)‐levoglucosenone (LGO), several bio‐based sp3‐rich amines containing up to four chiral centres have been readily prepared under aqueous conditions without using any catalysts, ligands, auxiliaries or resolutions.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Aza-michael Additions Tomentioning

confidence: 99%

Bio‐Based Chiral Amines via Aza‐Michael Additions to (–)‐Levoglucosenone Under Aqueous Conditions

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Menurut Zeynizadeh and Setamdideh (2005), reduksi sitronelal menjadi sitronelol dapat dilakukan dengan menggunakan perbandingan mol NaBH4 : sitronelal = 0,5 : 1 di dalam pelarut air.…”

Section: Pendahuluanunclassified

Substitution Reaction of Hydroxy of Citronellol With Chloride Using a Mixture of Ammonium Chloride and Sulphuric Acid

2016

View full text Add to dashboard Cite

ABSTRAKTelah dilakukan reaksi substitusi gugus hidroksi (-OH) pada sitronelol dengan klorida (-Cl) menggunakan campuran ammonium klorida (NH4Cl) dan asam sulfat (H2SO4). Sitronelol yang digunakan diperoleh dari reaksi reduksi sitronelal menggunakan natrium borohidrida (NaBH4) pada suhu ruang selama 30 menit. Reaksi substitusi dilakukan terhadap sitronelol hasil reduksi pada suhu 80 ºC dengan menggunakan variasi perbandingan mol sitronelol dan NH4Cl berturut-turut (1:1; 1:2; 1:3; dan 1:4). Identifikasi produk menggunakan kromatografi gas-spektrometri massa (GC-MS) menunjukkan produk substitusi berupa senyawa siklis 2-isopropil-5-metil-1-klorosikloheksana yang terbentuk pada perbandingan mol 1:4 dengan rendemen 64,49 %. Hasil analisis menggunakan spektrofotometer inframerah (IR) menunjukkan adanya vibrasi pada bilangan gelombang 763 cm -1 yang merupakan vibrasi khas C-Cl. Kata kunci : Sitronelol, Sitronelal, Substitusi ABSTRACTSubstitution reaction of hydroxy of citronellol with chloride using a mixture of ammonium chloride (NH4Cl) and sulphuric acid (H2SO4) has been conducted. The citronellol was obtained from the reduction of citronellal using sodium borohydride (NaBH4) at room temperature for 30 minutes. Substitution of hydroxy of citronellol with chloride ion was carried out at 80 o C and molarity ratio of citronellol and NH4Cl 1:1, 1:2; 1:3; and 1:4 respectively. Identification of the product by gas chromatography-mass spectrometry (GC-MS) showed that the substitution reaction produced 2-isopropyl-5-methyl-1-chlorocyclohexane compound with rendemen 64,49 % in mol ratio of 1:4. The infra red (IR) analysis showed that there was a vibration at wave number 763 cm -1 which is a typical C-Cl vibrations.

show abstract

“…Reduction of the aldehyde group 2-Chloroquinoline-3-carbaldehydes 2 were reduced with sodium borohydride NaBH 4 to (2-chloroquinolin-3-yl)methanol 92 either by using microwave irradiation, [69][70][71][72] or at room temperature. [73][74][75][76] Subsequently, compound 92 was converted into iodomethyl quinoline 93…”

Section: Scheme 33mentioning

confidence: 99%

2-Chloroquinoline-3-carbaldehydes: synthesis, reactions and applications

Abdel‐Wahab¹,

Khidre²,

Farahat³

et al. 2012

Arkivoc

View full text Add to dashboard Cite

This review summarizes the synthetic methods, reactions and biological applications of 2-chloroquinoline-3-carbaldehydes during the period from 1999 to 2011. The reactions are subdivided in groups that cover reactions at the chloro or aldehyde substituent and reactions which involve both groups. Most reaction types have been successfully applied and used in the production of biological active compounds.Keywords: Vilsmeier-Haack reaction, quinolines, aldehydes IntroductionInteresting pharmacological properties have been associated with 2-chloroquinoline-3-carbaldehydes and their derivatives.1,2 These compounds have shown antimicrobial, [1][2][3] antimalarial, 4,5 anti-inflammatory, 6-9 antitumor, 10,11 and anti-parasitic activity. 12 Despite this versatile importance, and in connection to our previous review articles about biologically active heterocyclic systems, 13 2-chloroquinoline-3-carbaldehydes have not been previously reviewed.The main objective of the present survey is to provide the synthesis, reactions, and biological applications of 2-chloroquinoline-3-carbaldehydes from 1999 to the end of 2011 and provide useful and up-to-date data for organic and medicinal chemists. Synthetic MethodsThere have been a number of practically important routes to synthesise of 2-chloroquinoline-3-carbaldehydes, e.g. (i) Vilsmeier-Haack reaction of acetanilides, (ii) oxidation of the corresponding alcohols. Vilsmeier-Haack reaction2-Chloroquinoline-3-carbaldehydes 2 were synthesized from acetanilides 1 via a VilsmeierHaack reaction either by traditional methods [14][15][16][17][18][19][20][21][22][23] or by microwave, 24 or ultrasonic irradiation (Scheme 1). 25Scheme 1 Reviews and Accounts ARKIVOC 2012 (i) 211-276Page 213 © ARKAT-USA, Inc. Oxidation of the corresponding alcohols(2-Chloroquinolin-3-yl)methanol 3 was oxidized to aldehyde 2 using a combination of diethyl diazene-1,2-dicarboxylate (DEAD) and catalytic ZnBr 2 in refluxing toluene (Scheme 2). 26Scheme 2 3 Chemical Reactions Substitution reactionsTreatment of 2-chloroquinoline-3-carbaldehydes 2 with prenyl thiolate or prenyl alcoholate 4 in the presence of sodium hydroxide or potassium t-butoxide, furnished S/O-prenyl aldehydes 5 in 72-84% yield, respectively. S/O-prenyl aldehyde 5, underwent imino Diels-Alder reactions with various substituted anilines in the presence of InCl 3 in acetonitrile resulting in the formation mixture of cis and trans products 7 and 8 in 55-71% yields by intramolecular cycloaddition reaction of the imine 6 generated in situ in the one pot-reaction (Scheme 3). 14 Scheme 3Knoevenagel hetero Diels-Alder reaction of 5 (X = O) with N,N'-dimethylbarbituric acid in water was carried out in the presence of piperidine at room temperature. The intermediate Knoevenagel adduct 9 was not isolated and allowed to cyclise at room temperature after 3 h stirring gave the cis-fused pentacyclic pyrano [2,3-b]quinoline derivatives 10 with high yield (80%) and diastereoselectivity (> 99%) (Scheme 4). 27 Scheme 4Recently, tetrahydrocyclopenta[c]acri...

show abstract

Water as a Green Solvent for Fast and Efficient Reduction of Carbonyl Compounds with NaBH₄under Microwave Irradiation

Cited by 26 publications

References 43 publications

Bio‐Based Chiral Amines via Aza‐Michael Additions to (–)‐Levoglucosenone Under Aqueous Conditions

Bio‐Based Chiral Amines via Aza‐Michael Additions to (–)‐Levoglucosenone Under Aqueous Conditions

Substitution Reaction of Hydroxy of Citronellol With Chloride Using a Mixture of Ammonium Chloride and Sulphuric Acid

2-Chloroquinoline-3-carbaldehydes: synthesis, reactions and applications

Contact Info

Product

Resources

About

Water as a Green Solvent for Fast and Efficient Reduction of Carbonyl Compounds with NaBH4under Microwave Irradiation

Cited by 26 publications

References 43 publications

Bio‐Based Chiral Amines via Aza‐Michael Additions to (–)‐Levoglucosenone Under Aqueous Conditions

Bio‐Based Chiral Amines via Aza‐Michael Additions to (–)‐Levoglucosenone Under Aqueous Conditions

Substitution Reaction of Hydroxy of Citronellol With Chloride Using a Mixture of Ammonium Chloride and Sulphuric Acid

2-Chloroquinoline-3-carbaldehydes: synthesis, reactions and applications

Contact Info

Product

Resources

About

Water as a Green Solvent for Fast and Efficient Reduction of Carbonyl Compounds with NaBH₄under Microwave Irradiation