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Regioselective N-alkylation of (2-chloroquinolin-3-yl) methanol with N-heterocyclic compounds using the Mitsunobu reagent

  • Selvaraj Roopan EMAIL logo , Fazlur-Rahman Khan and Jong Jin
Published/Copyright: March 16, 2011
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Chemical Papers
From the journal Chemical Papers Volume 65 Issue 3

Abstract

The Mitsunobu reaction is a well-established fundamental reaction and has been widely applied in organic synthesis. In this paper, under Mitsunobu conditions dehydration proceeds between (2-chloroquinolin-3-yl)methanol and nitrogen heterocyclic compounds such as quinazolinone, pyrimidone, 2-oxoquinoline in dry THF in the presence of triethylamine, triphenylphosphane and diethyl azodicarboxylate to give the corresponding products. As part of our recent research, we attempted to couple two N-heterocyclic compounds under Mitsunobu reaction conditions to provide efficient building blocks for natural product synthesis.

Keywords: Mitsunobu reaction; N-heterocyclic compounds; (2-chloroquinolin-3-yl)methanol; DEAD; P(Ph)3 ; THF

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Published Online: 2011-3-16
Published in Print: 2011-6-1

© 2011 Institute of Chemistry, Slovak Academy of Sciences

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https://doi.org/10.2478/s11696-011-0018-1
Keywords for this article
Mitsunobu reaction; N-heterocyclic compounds; (2-chloroquinolin-3-yl)methanol; DEAD; P(Ph)3; THF

Articles in the same Issue

  1. Steam-reforming of ethanol for hydrogen production
  2. Polymeric ionic liquid as a background electrolyte modifier enhancing the separation of inorganic anions by capillary electrophoresis
  3. Enantioselective extraction of terbutaline enantiomers with β-cyclodextrin derivatives as hydrophilic selectors
  4. Effective photocatalytic degradation of an azo dye over nanosized Ag/AgBr-modified TiO2 loaded on zeolite
  5. Photocatalytically-assisted electrochemical degradation of p-aminophenol in aqueous solutions using zeolite-supported TiO2 catalyst
  6. Spectroscopic investigations and physico-chemical characterization of newly synthesized mixed-ligand complexes of 2-methylbenzimidazole with metal ions
  7. Synthesis, molecular characterisation, and in vivo study of platinum(IV) coordination compounds against B16 mouse melanoma tumours
  8. Swelling properties of particles in amphoteric polyacrylamide dispersion
  9. Electronic structures and spectroscopic regularities of phenylene-modified SWCNTs
  10. An expeditious, environment-friendly, and microwave-assisted synthesis of 5-isatinylidenerhodanine derivatives
  11. Pd-catalysed conjugate addition of arylboronic acids to α,β-unsaturated ketones under microwave irradiation
  12. Regioselective N-alkylation of (2-chloroquinolin-3-yl) methanol with N-heterocyclic compounds using the Mitsunobu reagent
  13. Antimycobacterial 3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones and 3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones substituted on phenyl and benzoxazine moiety in position 6
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  15. Solubility of methane in pure non-ionic surfactants and pure and mixtures of linear alcohols at 298 K and 101.3 kPa
  16. Theoretical studies on polynitrobicyclo[1.1.1]pentanes in search of novel high energy density materials
  17. Insight into the degradation of a manganese(III)-citrate complex in aqueous solutions
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