Next Article in Journal
2-(4-(2-Chloroacetamido)-1-methyl-1H-pyrrole-2-carboxamido)ethyl Acetate
Previous Article in Journal
[7-(Fluoromethyl)-2-naphthyl]methanol
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molbank
Volume 2014
Issue 1
10.3390/M819
molbank-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles thumb_up
...
Endorse textsms
...
Comment
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

N,N-Dibenzyl-1-(1-[(4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)]-1H-1,2,3-triazol-4-yl)methanamine

by
Aouine Younas
,
El Hallaoui Abdelilah
and
Alami Anouar
*
Laboratoire de Chimie Organique, Faculté des Sciences Dhar El Mahraz, Université Sidi Mohamed Ben Abdellah, B.P. 1796 Fès-Atlas, 30003, Morocco
*
Author to whom correspondence should be addressed.
Molbank 2014, 2014(1), M819; https://doi.org/10.3390/M819
Submission received: 5 January 2014 / Accepted: 18 February 2014 / Published: 3 March 2014
Browse Figures
Versions Notes

Abstract

:
The title compound, N,N-dibenzyl-1-(1-[(4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)]-1H-1,2,3-triazol-4-yl)methanamine was synthesized in high yield by 1,3-dipolar cycloaddition reaction of 4-(azidomethyl)-4-methyl-2-phenyl-4,5-dihydrooxazole and N,N-dibenzylprop-2-yn-1-amine in toluene at reflux. The structure of this product was established on the basis of NMR spectroscopy (1H, 13C), Elemental Analysis and MS data.

Graphical Abstract

Triazoles constitute an important class of biologically active heterocyclic compounds that have received a great deal of attention since their discovery. Diverse compounds containing the 1,2,3-triazole moiety have a wide spectrum activities including antimicrobial activities [1,2], anti-HIV agents, antimicrobial, anticancer, antibacterial, antifungal, anti-tubercular compounds [3,4] and corrosion inhibitors [5].
Continuing our investigations in the use of oxazoline derivatives [6,7,8] in heterocyclic synthesis, we present in this short note a convenient and easy procedure for the preparation of N,N-dibenzyl-1-(1-[(4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)]-1H-1,2,3-triazol-4-yl)methanamine 3, a new oxazolinic precursors of heterocyclic amino acids.
For the first time, we prepared the terminal alkyne N,N-dibenzylprop-2-yn-1-amine 2 by the reaction of N-alkyaltion of propargyl bromide by dibenzylamine in anhydrous acetone at room temperature in the presence of K2CO3 as base [9]. The intermediate 2 is obtained with a 92% yield as colorless oil, and then it was submitted to cycloaddition reaction with azide 1.
This reaction leads normally to the formation of two regioisomers (1,4-isomer and 1,5-isomer) with prevalence of the 1,4-isomer [10]. We isolated after column chromatography on silica gel two isomers with a total yield of about 84%. The cycloadduct 3 was synthesized as shown in Scheme 1.
A mixture of 0.65 mmol of 4-(azidomethyl)-4-methyl-2-phenyl-4,5-dihydrooxazole 1 and 0.65 mmol of N,N-dibenzylprop-2-yn-1-amine 2 in 5mL of toluene, was heated at reflux with constant stirring for 72 h. After reaction, the solvent was evaporated under vacuum and the residue was extracted with ether. The organic layer was washed with water, dried with sodium sulfate (Na2SO4), and the solvent was removed. The products were purified by column chromatography on silica gel using ether/hexane (1/2) as eluent to afford pure products. The major product 3, the 1,4-isomer, was obtained as a white solid. The structures of the products were established on the basis of NMR spectroscopy (1H, 13C), Elemental analysis and MS data [11].
Description of the majority compound 3: White solid; Proportion of isomer = 80%; Rf (ether) = 0.51; Melting point: 100–102 °C.
1H-NMR (Bruker, 300.13 MHz, CDCl3): δ (ppm) 1.42 (3H, CH3, s); 3.37–3.47 (4H, dibenzyl, AB system, J = 13.47 Hz); 3.66–3.73 (2H, CH2N(Bn)2, AB system, J = 14.64 Hz); 4.06–4.52 (2H, 4,5-dihydrooxazole, AB system, J = 8.92 Hz); 4.45–4.53 (2H, CH2-triazole, AB system, J = 14.10 Hz); 7.18–7.91 (15Harom, m); 7.61 (1H51,2,3-triazole, s).
13C-NMR (Bruker, 75.47 MHz; CDCl3): δ (ppm) 25.1 (1C, CH3); 47.6 (1C, CH2N(Bn)2); 57.3 (2C, dibenzyl); 57.4 (1C, 4,5-dihydrooxazole); 70.7 (1C, CH2-triazole); 74.7 (1C, CH2(4,5-dihydrooxazole)); 132.0 and 150.3 (2C, C4 and C5 of 1,2,3-triazole); 124.6–139.5 (18Carom); 164.6 (1C, C=N of 4,5-dihydrooxazole).
Anal. calcd. for C28H29N5O: C, 74.47%; H, 6.47%; N, 15.51%. Found: C, 74.87%; H, 6.18%; N, 15.11%.
MS (EI): m/z (rel. int. %) = 451 (100%) (M+).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References and Notes

  1. Xu, W.; Song, B.; Bhadury, P.; Song, Y.; Hu, D. Synthesis and crystal structure of novel sulfone derivatives containing 1,2,4-triazole moieties. Molecules 2010, 15, 766–779. [Google Scholar] [CrossRef] [PubMed]
  2. Karabasanagouda, T.; Adhikari, A.V.; Shetty, N.S. Synthesis and antimicrobial activities of some novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines carrying thioalkyl and sulphonyl phenoxy moieties. Eur. J. Med. Chem. 2007, 42, 521–529. [Google Scholar] [CrossRef] [PubMed]
  3. Agalave, S.G.; Maujan, S.R.; Pore, V.S. Click chemistry: 1,2,3-Triazoles as pharmacophores. Chem. Asian J. 2011, 6, 2696–2718. [Google Scholar] [CrossRef] [PubMed]
  4. Ganesh, A. Potential biological activity of 1,4-sustituted-1H-[1,2,3]triazoles. Int. J. Chem. Sci. 2013, 11, 573–578. [Google Scholar]
  5. González-Olvera, R.; Espinoza-Vázquez, A.; Negrón-Silva, G.E.; Palomar-Pardavé, M.E.; Romero-Romo, M.A.; Santillan, R. Multicomponent click synthesis of new 1,2,3-triazole derivatives of pyrimidine nucleobases: promising acidic corrosion inhibitors for steel. Molecules 2013, 18, 15064–15079. [Google Scholar] [CrossRef] [PubMed]
  6. Atmani, A.; El Hajji, S.; El Hallaoui, A.; Roumestant, M.L.; Viallefont, P. From oxazolines to precursors of aminoacids. Synth.Commun. 1991, 21, 2383–2390. [Google Scholar] [CrossRef]
  7. Zaid, F.; El Hajji, S.; El Hallaoui, A.; Elachqar, A.; Kerbal, A.; Roumestant, M.L.; Viallefont, P. Synthesis of heterocyclic β-aminoalcohol precursors of heterocyclic α-aminoacids. Prep. Biochem. Biotechnol. 1998, 28, 137–153. [Google Scholar] [CrossRef] [PubMed]
  8. Zaid, F.; El Hajji, S.; El Hallaoui, A.; Elachqar, A.; Alami, A.; Roumestant, M.L.; Viallefont, P. Synthesis of heterocyclic α-aminoaldehyde and α-aminoacid analogues of Histidines. Prep. Biochem. Biotechnol. 1998, 28, 155–165. [Google Scholar] [CrossRef] [PubMed]
  9. Aouine, Y.; Faraj, H.; Alami, A.; El Hallaoui, A.; Elachqar, A.; El Hajji, S.; Kerbal, A.; Labriti, B.; Martinez, J.; Rolland, V. Synthesis of new compounds, precursors of biheterocyclic amino acids. J. Mar. Chim. Heterocycl. 2008, 7, 44–49. [Google Scholar]
  10. Huisgen, R. Kinetics and mechanism of 1,3-dipolar cycloadditions. Angew. Chem. Int. Ed. 1963, 2, 633–645. [Google Scholar] [CrossRef]
  11. Description of the minority compound: Yellow oil; Rf (ether) = 0.63. 1H-NMR (Bruker, 300.13 MHz, CDCl3): δ (ppm) 1.30 (3H, CH3, s); 3.46–3.56 (4H, dibenzyl, AB system, J = 13.45 Hz); 3.63–3.92 (2H, CH2N(Bn)2, AB system, J = 14.49 Hz); 5.04–5.65 (2H, 4,5-dihydrooxazole, AB system, J = 8.91 Hz); 6.46 (2H, CH2-triazole, s); 7.06–7.91 (15Harom, m); 7.58 (1H41,2,3-triazole, s). 13C-NMR (Bruker, 75.47 MHz; CDCl3): δ (ppm) 25.1 (1C, CH3); 46.7 (1C, CH2N(Bn)2); 55.1 (1C, 4,5-dihydrooxazole); 58.3 (2C, dibenzyl); 71.2 (1C, CH2-triazole); 75.5 (1C, CH2(4,5-dihydrooxazole)); 131.7 and 150.0 (2C, C4 and C5 of 1,2,3-triazole); 127.0–138.3 (18Carom); 164.0 (1C, C=N of 4,5-dihydrooxazole). MS (EI): m/z (rel. int. %) = 451.2 (100%) (M+).
Molbank 2014 m819 sch001 550
Scheme 1. Synthesis of compounds 3.
Scheme 1. Synthesis of compounds 3.
Molbank 2014 m819 sch001

Share and Cite

MDPI and ACS Style

Younas, A.; Abdelilah, E.H.; Anouar, A. N,N-Dibenzyl-1-(1-[(4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)]-1H-1,2,3-triazol-4-yl)methanamine. Molbank 2014, 2014, M819. https://doi.org/10.3390/M819

AMA Style

Younas A, Abdelilah EH, Anouar A. N,N-Dibenzyl-1-(1-[(4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)]-1H-1,2,3-triazol-4-yl)methanamine. Molbank. 2014; 2014(1):M819. https://doi.org/10.3390/M819

Chicago/Turabian Style

Younas, Aouine, El Hallaoui Abdelilah, and Alami Anouar. 2014. "N,N-Dibenzyl-1-(1-[(4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)]-1H-1,2,3-triazol-4-yl)methanamine" Molbank 2014, no. 1: M819. https://doi.org/10.3390/M819

APA Style

Younas, A., Abdelilah, E. H., & Anouar, A. (2014). N,N-Dibenzyl-1-(1-[(4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)]-1H-1,2,3-triazol-4-yl)methanamine. Molbank, 2014(1), M819. https://doi.org/10.3390/M819

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Metrics

Back to TopTop