A simple and efficient synthesis of2-(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
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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
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).
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).
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).
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.