Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 4
347
Views
12
CrossRef citations to date
0
Altmetric
Original Articles

Electro-Organic Synthesis of 2-Amino-3-cyano-benzofuran Derivatives Using Hydroquinones and Malononitrile

, , , , &
Pages 561-568 | Received 19 Oct 2009, Published online: 02 Feb 2011

REFERENCES

  • Dean, F. M., 1973. Total Synthesis of Natural Products. New York: Wiley; 1973.
  • Kumar, V., Ackerman, J. H., Alexander, M. D., Bell, M. R., Christiansen, R. G., Dung, J. S., Jaeger, E. P., Herrmann, Jr., J. L., Krolski, M. E., McKloskey, P., Batzold, F. H., Juniewicz, P. E., Reel, J., Snyder, B. W., and Winneker, R. C., 1994. Androgen receptor affinity of 5′-acyl furanosteroids, J. Med. Chem. 37 (1994), pp. 4227–4236.
  • Ohemeng, K. A., Appollina, M. A., Nguyen, V. N., Schwender, C. F., Singer, M., Steber, M., Ansell, J., Argentieri, D., and Hageman, W., 1994. Synthesis and 5-lipoxygenase inhibitory activities of some novel 2-substituted 5-benzofuran hydroxamic acids, J. Med. Chem. 37 (1994), pp. 3663–3667.
  • Nagahara, T., Yokoyama, Y., Inamura, K., Katakura, S., Komoriya, S., Yamaguchi, H., Hara, T., and Iwamoto, M., 1994. Dibasic (amidinoaryl)propanoic acid derivatives as novel blood coagulation factor Xa inhibitors, J. Med. Chem. 37 (1994), pp. 1200–1207.
  • Yang, Z., Liu, H. B., Lee, C. M., Chang, H. M., and Wong, H. N. C., 1992. Compounds from Danshen, part 7: Regioselective introduction of carbon-3 substituents to 5-alkyl-7-methoxy-2-phenylbenzo[b]furans: Synthesis of a novel adenosine A1 receptor ligand and its derivatives, J. Org. Chem. 57 (1992), pp. 7248–7257.
  • Gubin, J., Vogelaer, H., Inion, H., Houben, C., Lucchetti, J., Mahaux, J., Rosseels, G., Peiren, M., Client, M., Polster, P., and Chatelain, P., 1993. Novel heterocyclic analogs of the new potent class of calcium entry blockers: 1-[[4-(Aminoalkoxy)phenyl]sulfonyl]indolizines, J. Med. Chem. 36 (1993), pp. 1425–1433.
  • Hayakawa, I., Shioya, R., Agastuma, T., Furokawa, H., and Sugano, Y., 2004. Thienopyridine and benzofuran derivatives as potent anti-tumor agents possessing different structure–activity relationships, Bioorg. Med. Chem. Lett. 14 (2004), pp. 3411–3414.
  • Gaszner, P., and Miklya, I., 2006. Major depression and the synthetic enhancer substances, (−)-deprenyl and R-(-)-1-(benzofuran-2-yl)-2-propylaminopentane, Prog. Neuro-Psychopharmacol. Biol. Psychiatry 30 (2006), pp. 5–14.
  • Ono, M., Kawashima, H., Nonaka, A., Kawai, T., Haratake, M., Mori, H., Kung, M.-P., Kung, H. F., Saji, H., and Nakayama, M., 2006. Novel benzofuran derivatives for PET imaging of β-amyloid plaques in Alzheimer's disease brains, J. Med. Chem. 49 (2006), pp. 2725–2730.
  • Yue, D., Yao, T., and Larock, R. C., 2005. Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization, J. Org. Chem. 70 (2005), pp. 10292–10296.
  • Nakamura, I., Mizushima, Y., and Yamamoto, Y., 2005. Synthesis of 2,3-disubstituted benzofurans by platinum−olefin-catalyzed carboalkoxylation of o-alkynylphenyl acetals, J. Am. Chem. Soc. 127 (2005), pp. 15022–15023.
  • Chen, C.-Y.Dormer, P. G., , 2005. Synthesis of benzo[b]furans via CuI-catalyzed ring closure, J. Org. Chem. 70 (2005), pp. 6964–6967.
  • Carril, M., San Martin, R., Tellitu, I., and Dominguez, E., 2006. On-water chemistry: Copper-catalyzed straightforward synthesis of benzo[b]furan derivatives in neat water, Org. Lett. 8 (2006), pp. 1467–1470.
  • Kumar, M. P., and Liu, R.-S., 2006. Zn(OTf)2-catalyzed cyclization of proparyl alcohols with anilines, phenols, and amides for synthesis of indoles, benzofurans, and oxazoles through different annulation mechanisms, J. Org. Chem. 71 (2006), pp. 4951–4955.
  • Anderson, K. W., Ikawa, T., Tundel, R. E., and Buchwald, S. L., 2006. The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans, J. Am. Chem. Soc. 128 (2006), pp. 10694–10695.
  • Lu, B., Wang, B., Zhang, Y., and Ma, D., 2007. CuI-catalyzed domino process to 2,3-disubstituted benzofurans from 1-bromo-2-iodobenzenes and β-keto esters, J. Org. Chem. 72 (2007), pp. 5337–5341.
  • De Luca, L., Giacomelli, G., and Nieddu, G., 2007. A facile approach to the synthesis of chiral 2-substituted benzofurans, J. Org. Chem. 72 (2007), pp. 3955–3957.
  • Ishikawa, T., Miyahara, T., Asakura, M., Higuchi, S., Miyauchi, Y., and Saito, S., 2005. One-pot multistep synthesis of 4-acetoxy-2-amino-3-arylbenzofurans from 1-aryl-2-nitroethylenes and cyclohexane-1,3-diones, Org. Lett. 7 (2005), pp. 1211–1214.
  • Hosseiny Davarani, S. S., Fakhari, A. R., Shaabani, A., Ahmar, H., Maleki, A., and Sheijooni Fumani, N. A facile electrochemical method for the synthesis of phenazine derivatives via an ECECC pathway., 2008. Tetrahedron Lett. 49 (2008), pp. 5622–5624.
  • Fakhari, A. R., Hasheminasab, K., Ahmar, H., and Alizadeh, A., 2008. An efficient synthesis of thio- and thiazoloquinazolinones by the electrochemical oxidation of catechols in the presence of 2-mercapto-4(3H)-quinazolinone, Synthesis 24 (2008), pp. 3963–3966.
  • Hosseiny Davarani, S. S., Fakhari, A. R., Sheijooni Fumani, N., and Kalate-bojdi, M., 2008. Electrochemical synthesis of new benzodifurans, Electrochem. Commun. 10 (2008), pp. 1765–1768.
  • Izutsu, K., 2002. Electrochemistry in Nonaqueous Solutions. Weinheim: Wiley; 2002.
  • Nematollahi, D., Amani, A., and Tammari, E., 2007. Electrosynthesis of symmetric and highly conjugated benzofuran via a unique ECECCC electrochemical mechanism: Evidence for predominance of electrochemical oxidation versus intramolecular cyclization, J. Org. Chem. 72 (2007), pp. 3646–3651.
  • Shaabani, A., Rezayan, A. H., Sarvary, A., Rahmati, A., and Khavasi, H. R., 2008. Pyridine-catalyzed reaction of tetracyanoethylene and activated 1,3-dicarbonyl CH-acid compounds: A rapid and efficient synthesis of pyran annulated heterocyclic systems, Catal. Commun. 9 (2008), pp. 1082–1086.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.