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Short Note

2-(3-thienyl)-2,3-dihydrofuro[2,3-b]quinoxaline

Laboratoire de Chimie Organique Hétérocyclique, Pôle de compétences Pharmacochimie, Université Mohammed V-Agdal, BP: 1014 Avenue Ibn Batouta, Rabat, Morocco
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Author to whom correspondence should be addressed.
Molbank 2007, 2007(2), M536; https://doi.org/10.3390/M536
Submission received: 9 November 2006 / Revised: 4 December 2006 / Published: 31 May 2007
Heterocyclic compounds particularly five and six membered ring compounds have occupied a prominent place among various classes of organic compounds for their diverse biological activities. Among a wide variety of heterocycles that have been explored for developing pharmaceutically important molecules. Quinoxaline and thiophene have played an important role in medicinal chemistry. Some of them have received considerable attention as potential antimicrobial1 [2], and antiviral [3,4].
The aim of this work is to describe the synthesis of a novel compound entitled 2-(3-thienyl)-2,3-dihydrofuro[2,3-b]quinoxaline.
Molbank 2007 m536 i001
The 3-methylquinoxalin-2(1H)-one 1 (1.25 mmol, 2 g) and 3-formyl-thiophene 2 (3.75 mmol, 4.8 mL) were heated in a bath oil at 150 °C for 3h. After cooling of the reaction, the crude product was recrystallized from ethanol to obtain compound 3.
This compound was obtained in 65 % yield.
Melting point: > 250 °C.
¹H-NMR (300 MHz, DMSO-d6): 3.17, 3.20 (m, 2H, HaHb, JAB = 14.7 Hz, JAX = JBX = 7.2 Hz); 4.28 (q, 1H, Hx, JAX = JBX = 7.2 Hz); 7.05-7.62 (m, 7H, HAr).
¹³C-NMR (300 MHz, DMSO-d6): 35.5 (CH); 48.5 (CH2); 115.4, 120.6, 123.3, 126.0, 127.8, 128.3, 129.7 (CHAr); 131.9, 132.0, 146.4, 155.1, 160.8 (Cq).
MS (EI): M+(m/z = 254, 46%); 143 (100%).
Elemental analysis: Calculated for C14H10N2OS: C, 66.12 %; H, 3.96 %; N, 11.02 %; Found: C, 66.22 %; H, 4.01 %; N, 11.12 %;

Supplementary materials

Supplementary File 1

References

  1. Carta, A.; Paglietti, G.; Nikookar, M.E.R.; Sanna, P.; Sechi, L.; Zanetti, S. Eur. J. Med. Chem. 2002, 37, 355. [PubMed]
  2. Carta, A.; Loriga, M.; Zanetti, S.; Sechi, L.A. Il Farmaco 2003, 58, 1251. [PubMed]
  3. Fonseca, T.; Gigante, B.; Marques, M.M.; Gilchrist, T.L.; De Clercq, E. Bioorg. Med. Chem. 2004, 12, 103. [PubMed]
  4. Sehlstedt, U.; Aich, P.; Bergman, J.; Vallberg, H.; Nordén, B.; Gräslund, A. J. Mol. Bio. 1998, 278, 31.

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MDPI and ACS Style

Anothane, C.A.; Essassi, E.M. 2-(3-thienyl)-2,3-dihydrofuro[2,3-b]quinoxaline. Molbank 2007, 2007, M536. https://doi.org/10.3390/M536

AMA Style

Anothane CA, Essassi EM. 2-(3-thienyl)-2,3-dihydrofuro[2,3-b]quinoxaline. Molbank. 2007; 2007(2):M536. https://doi.org/10.3390/M536

Chicago/Turabian Style

Anothane, Caleb Ahoya, and El Mokhtar Essassi. 2007. "2-(3-thienyl)-2,3-dihydrofuro[2,3-b]quinoxaline" Molbank 2007, no. 2: M536. https://doi.org/10.3390/M536

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