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1-(ethoxycarbonylmethyl)-3-(1’-tolyl-3’-(ethoxycarbonyl)5’-hydroxypyrazolyl)-2-oxo quinoxaline
 
 
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Volume 2006
Issue 2
10.3390/M473
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Short Note

1-ethoxycarbonylmethyl-3-(ethoxycarbonylmethylene)-2-oxo quinoxaline

by
Souad Ferfra
,
Noureddine H. Ahabchane
and
El Mokhtar Essassi
*
Laboratoire de Chimie Organique Hétérocyclique, Faculté des Sciences, BP 1014, Avenue Ibn Batouta, Rabat, Maroc
*
Author to whom correspondence should be addressed.
Molbank 2006, 2006(2), M473; https://doi.org/10.3390/M473
Submission received: 13 February 2006 / Accepted: 18 February 2006 / Published: 28 February 2006
Versions Notes

Molbank 2006 m473 i001
The compound 3, which exists in tautomeric equilibria between enamine (form A) and methylene imine (form B), was prepared by addition of ethoxycarbonylmethyl chloride 2 (1.23g, 0.01 mol) to a solution of 3-(ethoxycarbonylmethylene)-2-oxo quinoxaline, 1 [1] (2.32 g, 0.01 mol) in 60 ml DMF, K2CO3 (1.38g, 0.01mol) and triethylbenzylammonium chloride (0.001 mol). The mixture was stirred for 24 hours at room temperature. After filtration, the solvent was evaporated and the residue was recrystallized from ethanol affording 3 in 90% yield.
Melting point: 154-156°C.
IR (KBr, cm-1) : 1650 ( nN-C=O); 1720 (nN-C=O).
1H-NMR (250 MHz, CDCl3): δ= 11.20 (0.5H, s, NH, form A); 7.87-6.82 (8H, m, ar); 5.83 (0.5H, s, =CH, form A); 5.01 (1H, s, NCH2); 4.89 (1H, s, NCH2); 4.21 (8H, m, CH2); 3.95 (2H, s, CH2, form B); 1.27 (12H , m, CH3).
13C-NMR (250MHz, CDCl3): δ= 170.7 (Cq); 169.3 (Cq); 167.3 (Cq); 166.9 (Cq); 156.4 (Cq); 154.4 (Cq); 142.5 (Cq); 132.7 (Cq); 130.6 (CHar); 130.4 (CHar); 126.0 (Cq); 124.5 (CHar); 124.0 (CHar); 122.5 (CHar); 115.4 (CHar); 113.8 (CHar); 113.2 (CHar); 86.7 (=CH form A); 62.1 (CH2); 62.0 (CH2); 62.2 (CH2); 59.9 (CH2); 44.0 (NCH2); 43.6 (NCH2); 40.7 (CH2 form B); 14.4 (CH3); 14.1 (CH3).
MS (I.E): 318 [M+].

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Reference

  1. Kurasawa, Y.; Takada, A. Heterocycles. 1985; 23, N°8. [Google Scholar]
  • Sample Availability: Available from MDPI.

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MDPI and ACS Style

Ferfra, S.; Ahabchane, N.H.; Essassi, E.M. 1-ethoxycarbonylmethyl-3-(ethoxycarbonylmethylene)-2-oxo quinoxaline. Molbank 2006, 2006, M473. https://doi.org/10.3390/M473

AMA Style

Ferfra S, Ahabchane NH, Essassi EM. 1-ethoxycarbonylmethyl-3-(ethoxycarbonylmethylene)-2-oxo quinoxaline. Molbank. 2006; 2006(2):M473. https://doi.org/10.3390/M473

Chicago/Turabian Style

Ferfra, Souad, Noureddine H. Ahabchane, and El Mokhtar Essassi. 2006. "1-ethoxycarbonylmethyl-3-(ethoxycarbonylmethylene)-2-oxo quinoxaline" Molbank 2006, no. 2: M473. https://doi.org/10.3390/M473

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