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A Novel And Facile Synthesis of 2 (Cyclohexylamino) 6,7 Dihydro 3 Aryl Benzofuran 4(5h) Ones By One Pot Three Component Reaction

Year 2010, Volume: 23 Issue: 4, 429 - 433, 19.03.2010

Abstract

A simple and efficient synthesis of  2-(cyclohexylamino)- 6,7-dihydro-3-aryl benzofuran-4(5H)-ones derivatives was achieved  via a one-pot three –component reaction of  cyclohexylisocyanide, aldehydes, and dimedone or 1,3-cyclohexanedione in DMF for 2 hr with good yields.

 Keywords: Cyclohexyl isocyanide, dimedone, 1,3- cyclohexanedione, one-pot three component reaction

References

  • Dean, F.M., “Advances in Heterocyclic Chemistry”; Katritzky, A.R., Ed.; Academic; New York ; 30: 167-238 (1982)
  • Nakanishi, K., “Natural Products Chemistry”; Kodansha; Tokyo, (1974).
  • Strenbach, D.D., Rossana, D.M.,”Intramolecular diels-alder reactions of the furan diene: substituent and solvent effects“, Tetrahedron Lett., 23: 303(1982).
  • Jung, M.E., Street, L.,”Synthetic studies on the avermectins: substituent effects on intramolecular Diels-Alder reactions of N-furfurylacrylamides and further reactions of the cycloadducts”, J. Am. Chem. Soc., 106: 8327 (1984).
  • Best, W.M., Wege, D.,” Intramolecular diels-alder reactions of benzynes application to the total synthesis of mansonone E”, Tetrahedron Lett., 22: 4877 (1981).
  • Zhu, J., Bienayme, H.,“ Multicomponent Reactions“, Wiely-VCH, Weinheim, (2005).
  • Litvinov, V.P.,”Multicomponent cascade heterocyclisation as a promising route to targeted synthesis of polyfunctional pyridines“, Russ. Chem. Rev., 72: 69 (2003).
  • Ugi, I., Dömling, A., Hörl, W.,”Multicomponent Reactions“, Endeavour., 18: 115 (1994).
  • Tietze, L.F., Modi, A.,”Multicomponent domino reactions for the synthesis of biologically active natural products and drugs“, Med. Res. Rev., 20: 304 (2000).
  • Ugi, I., Dömling, A., Werner, B.,”Since 1995 the new chemistry of multicomponent reactions and their libraries, including their heterocyclic chemistry“, J. Heterocycl. Chem., 37: 647 (2000).
  • Passerini, M.,”Passerini Reaction“, Gazz Chim. Ital., 52: 432 (1992).
  • Cristau, P.; Vors, J. P.; Zhu., “Rapid synthesis of cyclopeptide alkaloid-like para-cyclophanes” , J. QSAR Comb. Sci., 25: 519 (2006).
  • Ugi, I., Meyr, R., Fetzer, U., Steinbrückner, C., “Versuche mit Isonitrilen” , Angew .Chem., 71: 386 (1959).
  • Ugi, I., Steinbrückner, C.,”Über ein neues Kondensations-Prinzip“, Angew. Chem., 72: 267 (1960).
  • Murakami, M.,”New Catalyzed Three-Component Cycloadditions for the Synthesis of Eight- Membered Carbocycles“, Angew. Chem. Int. Ed. 42: 718 (2003).
  • Bienayme, H., Hulme, C., Oddon, G., Schmitt, P.,”Maximizing synthetic efficiency: Multi- component transformations lead the way“, Chem.Eur. J., 6: 3321 (2000).
  • Dömling, A.,”Recent advances in isocyanide- based multicomponent chemistry“, Curr. Opin. Chem. Biol., 6: 306 (2002).
  • Hulme, C., Gore, V.,” “Multi-component
  • Reactions: Emerging Chemistry in Drug Discovery”
  • ‘From Xylocain to Crixivan’“, Curr. Med. Chem., 10: 51 (2003).
  • Orru, R. V. A., De Greef, M.,”Recent Advances in Solution-Phase Multicomponent Methodology for the Synthesis of Heterocyclic Compounds“, Synthesis, 1471 (2003).
  • Balme, G., Bossharth, E., Monteiro, N.,”Pd- Assisted Multicomponent Synthesis of Heterocycles“, Eur. J. Org.Chem. 21: 4101 (2003).
  • Wangelin, J.C., Neumann, A., Gordes, H., Klaus, D., Strübing, S., Beller, D.M.,”Multicomponent Coupling Reactions for Organic Synthesis: Chemoselective Reactions with Amide–Aldehyde Mixtures“, Chem. Eur. J., 9: 4286 (2003).
  • Dömling, A., Ugi, I.,”Multicomponent Reactions with Isocyanides“, Angew. Chem. Int. Ed. 39, 3168 (2000).
  • Marcaccini, S., Torroba, T.,”The use of isocyanides in heterocyclic synthesis. A review“, Org. Prep. Proced. Int., 25: 141(1993).
  • Ugi, I., Lohberger, S., Karl, R.. “In Comprehensive Organic Synthesis;” Trost, B. M. Fleming, I., Eds.; Pergamon: New York,; 2 (4-6): 1083 (1993).
  • Bamoharram, F.F., Heravi, M.M., Roshani, M., “Catalytic Method for Synthesis of Aspirin by a Green, Efficient and Recyclable Solid Acid Catalyst (Preyssler’s Anion) at Room Temperature” , J. Chin.Chem. Soc., 54: 1017 (2007). [26]
  • Heravi, M.M., Bakhtiari, K., Oskooie,
  • H.A.,”Communication: KHSO Supported onto
  • Bentonite, A Versatile Reagent for Aromatization
  • of Hantzsch 1,4-Dihydropyridines“, J. Chin.
  • Chem. Soc., 54, 579 (2007).
  • Heravi, M.M., Oskooie, H. A., Baghernejad, B.,”Facile, Regioselective and Green Synthesis of Ortho-nitrophenoles Using NaNO2, KHSO4”, J. Chin.Chem. Soc., 54:767 (2007).
Year 2010, Volume: 23 Issue: 4, 429 - 433, 19.03.2010

Abstract

References

  • Dean, F.M., “Advances in Heterocyclic Chemistry”; Katritzky, A.R., Ed.; Academic; New York ; 30: 167-238 (1982)
  • Nakanishi, K., “Natural Products Chemistry”; Kodansha; Tokyo, (1974).
  • Strenbach, D.D., Rossana, D.M.,”Intramolecular diels-alder reactions of the furan diene: substituent and solvent effects“, Tetrahedron Lett., 23: 303(1982).
  • Jung, M.E., Street, L.,”Synthetic studies on the avermectins: substituent effects on intramolecular Diels-Alder reactions of N-furfurylacrylamides and further reactions of the cycloadducts”, J. Am. Chem. Soc., 106: 8327 (1984).
  • Best, W.M., Wege, D.,” Intramolecular diels-alder reactions of benzynes application to the total synthesis of mansonone E”, Tetrahedron Lett., 22: 4877 (1981).
  • Zhu, J., Bienayme, H.,“ Multicomponent Reactions“, Wiely-VCH, Weinheim, (2005).
  • Litvinov, V.P.,”Multicomponent cascade heterocyclisation as a promising route to targeted synthesis of polyfunctional pyridines“, Russ. Chem. Rev., 72: 69 (2003).
  • Ugi, I., Dömling, A., Hörl, W.,”Multicomponent Reactions“, Endeavour., 18: 115 (1994).
  • Tietze, L.F., Modi, A.,”Multicomponent domino reactions for the synthesis of biologically active natural products and drugs“, Med. Res. Rev., 20: 304 (2000).
  • Ugi, I., Dömling, A., Werner, B.,”Since 1995 the new chemistry of multicomponent reactions and their libraries, including their heterocyclic chemistry“, J. Heterocycl. Chem., 37: 647 (2000).
  • Passerini, M.,”Passerini Reaction“, Gazz Chim. Ital., 52: 432 (1992).
  • Cristau, P.; Vors, J. P.; Zhu., “Rapid synthesis of cyclopeptide alkaloid-like para-cyclophanes” , J. QSAR Comb. Sci., 25: 519 (2006).
  • Ugi, I., Meyr, R., Fetzer, U., Steinbrückner, C., “Versuche mit Isonitrilen” , Angew .Chem., 71: 386 (1959).
  • Ugi, I., Steinbrückner, C.,”Über ein neues Kondensations-Prinzip“, Angew. Chem., 72: 267 (1960).
  • Murakami, M.,”New Catalyzed Three-Component Cycloadditions for the Synthesis of Eight- Membered Carbocycles“, Angew. Chem. Int. Ed. 42: 718 (2003).
  • Bienayme, H., Hulme, C., Oddon, G., Schmitt, P.,”Maximizing synthetic efficiency: Multi- component transformations lead the way“, Chem.Eur. J., 6: 3321 (2000).
  • Dömling, A.,”Recent advances in isocyanide- based multicomponent chemistry“, Curr. Opin. Chem. Biol., 6: 306 (2002).
  • Hulme, C., Gore, V.,” “Multi-component
  • Reactions: Emerging Chemistry in Drug Discovery”
  • ‘From Xylocain to Crixivan’“, Curr. Med. Chem., 10: 51 (2003).
  • Orru, R. V. A., De Greef, M.,”Recent Advances in Solution-Phase Multicomponent Methodology for the Synthesis of Heterocyclic Compounds“, Synthesis, 1471 (2003).
  • Balme, G., Bossharth, E., Monteiro, N.,”Pd- Assisted Multicomponent Synthesis of Heterocycles“, Eur. J. Org.Chem. 21: 4101 (2003).
  • Wangelin, J.C., Neumann, A., Gordes, H., Klaus, D., Strübing, S., Beller, D.M.,”Multicomponent Coupling Reactions for Organic Synthesis: Chemoselective Reactions with Amide–Aldehyde Mixtures“, Chem. Eur. J., 9: 4286 (2003).
  • Dömling, A., Ugi, I.,”Multicomponent Reactions with Isocyanides“, Angew. Chem. Int. Ed. 39, 3168 (2000).
  • Marcaccini, S., Torroba, T.,”The use of isocyanides in heterocyclic synthesis. A review“, Org. Prep. Proced. Int., 25: 141(1993).
  • Ugi, I., Lohberger, S., Karl, R.. “In Comprehensive Organic Synthesis;” Trost, B. M. Fleming, I., Eds.; Pergamon: New York,; 2 (4-6): 1083 (1993).
  • Bamoharram, F.F., Heravi, M.M., Roshani, M., “Catalytic Method for Synthesis of Aspirin by a Green, Efficient and Recyclable Solid Acid Catalyst (Preyssler’s Anion) at Room Temperature” , J. Chin.Chem. Soc., 54: 1017 (2007). [26]
  • Heravi, M.M., Bakhtiari, K., Oskooie,
  • H.A.,”Communication: KHSO Supported onto
  • Bentonite, A Versatile Reagent for Aromatization
  • of Hantzsch 1,4-Dihydropyridines“, J. Chin.
  • Chem. Soc., 54, 579 (2007).
  • Heravi, M.M., Oskooie, H. A., Baghernejad, B.,”Facile, Regioselective and Green Synthesis of Ortho-nitrophenoles Using NaNO2, KHSO4”, J. Chin.Chem. Soc., 54:767 (2007).
There are 33 citations in total.

Details

Primary Language English
Journal Section Chemistry
Authors

Bita Baghernejad This is me

Rahim Hekmatshoar

Majid Heravi This is me

Publication Date March 19, 2010
Published in Issue Year 2010 Volume: 23 Issue: 4

Cite

APA Baghernejad, B., Hekmatshoar, R., & Heravi, M. (2010). A Novel And Facile Synthesis of 2 (Cyclohexylamino) 6,7 Dihydro 3 Aryl Benzofuran 4(5h) Ones By One Pot Three Component Reaction. Gazi University Journal of Science, 23(4), 429-433.
AMA Baghernejad B, Hekmatshoar R, Heravi M. A Novel And Facile Synthesis of 2 (Cyclohexylamino) 6,7 Dihydro 3 Aryl Benzofuran 4(5h) Ones By One Pot Three Component Reaction. Gazi University Journal of Science. September 2010;23(4):429-433.
Chicago Baghernejad, Bita, Rahim Hekmatshoar, and Majid Heravi. “A Novel And Facile Synthesis of 2 (Cyclohexylamino) 6,7 Dihydro 3 Aryl Benzofuran 4(5h) Ones By One Pot Three Component Reaction”. Gazi University Journal of Science 23, no. 4 (September 2010): 429-33.
EndNote Baghernejad B, Hekmatshoar R, Heravi M (September 1, 2010) A Novel And Facile Synthesis of 2 (Cyclohexylamino) 6,7 Dihydro 3 Aryl Benzofuran 4(5h) Ones By One Pot Three Component Reaction. Gazi University Journal of Science 23 4 429–433.
IEEE B. Baghernejad, R. Hekmatshoar, and M. Heravi, “A Novel And Facile Synthesis of 2 (Cyclohexylamino) 6,7 Dihydro 3 Aryl Benzofuran 4(5h) Ones By One Pot Three Component Reaction”, Gazi University Journal of Science, vol. 23, no. 4, pp. 429–433, 2010.
ISNAD Baghernejad, Bita et al. “A Novel And Facile Synthesis of 2 (Cyclohexylamino) 6,7 Dihydro 3 Aryl Benzofuran 4(5h) Ones By One Pot Three Component Reaction”. Gazi University Journal of Science 23/4 (September 2010), 429-433.
JAMA Baghernejad B, Hekmatshoar R, Heravi M. A Novel And Facile Synthesis of 2 (Cyclohexylamino) 6,7 Dihydro 3 Aryl Benzofuran 4(5h) Ones By One Pot Three Component Reaction. Gazi University Journal of Science. 2010;23:429–433.
MLA Baghernejad, Bita et al. “A Novel And Facile Synthesis of 2 (Cyclohexylamino) 6,7 Dihydro 3 Aryl Benzofuran 4(5h) Ones By One Pot Three Component Reaction”. Gazi University Journal of Science, vol. 23, no. 4, 2010, pp. 429-33.
Vancouver Baghernejad B, Hekmatshoar R, Heravi M. A Novel And Facile Synthesis of 2 (Cyclohexylamino) 6,7 Dihydro 3 Aryl Benzofuran 4(5h) Ones By One Pot Three Component Reaction. Gazi University Journal of Science. 2010;23(4):429-33.