NaBH4/NaHSO4·H2O a Heterogeneous Acidic System for a Mild and Convenient Reduction of Carbonyl Compounds under Protic Condition

Zeynizadeh, Behzad; Behyar, Tarifeh

doi:10.1515/znb-2005-0417

Cited by 10 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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

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

show abstract

“…3) and 2-hydroxy-5methylbenzaldehyde96 were synthesized according to the literature procedures. 2-Hydroxy-5-methylbenzyl alcohol, 5-bromo-2-hydroxybenzyl alcohol97 were synthesized according to modi-ed literature procedures. 2-Hydroxybenzyl alcohol was puried by column chromatography (on silica gel using an ethyl acetate/ n-hexane mixture (20/80) as eluent) before usage.…”

mentioning

confidence: 99%

Porous Ge@C materials via twin polymerization of germanium(ii) salicyl alcoholates for Li-ion batteries

et al. 2016

View full text Add to dashboard Cite

show abstract

NaBH₄/NaHSO₄×H₂O, a Heterogeneous Acidic System for a Mild and Convenient Reduction of Carbonyl Compounds under Protic Condition.

Zeynizadeh

Behyar

2005

ChemInform

View full text Add to dashboard Cite

NaBH₄/NaHSO₄·H₂O a Heterogeneous Acidic System for a Mild and Convenient Reduction of Carbonyl Compounds under Protic Condition

Cited by 10 publications

References 0 publications

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

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

Porous Ge@C materials via twin polymerization of germanium(ii) salicyl alcoholates for Li-ion batteries

NaBH₄/NaHSO₄×H₂O, a Heterogeneous Acidic System for a Mild and Convenient Reduction of Carbonyl Compounds under Protic Condition.

Contact Info

Product

Resources

About

NaBH4/NaHSO4·H2O a Heterogeneous Acidic System for a Mild and Convenient Reduction of Carbonyl Compounds under Protic Condition

Cited by 10 publications

References 0 publications

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

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

Porous Ge@C materials via twin polymerization of germanium(ii) salicyl alcoholates for Li-ion batteries