SavedAdd your journal

Journals / Gazi University Journal of Science / 2010 / Volume: 23 Issue: 4

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

Bita Baghernejad
Rahim Hekmatshoar
Majid Heravi
Pages
—
Publication Date
2010-03-19
DOI
—
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Normal 0 21 false false false TR X-NONE X-NONE 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

📌 3 Key Takeaways

🎯
Objective & Hypothesis:Normal 0 21 false false false TR X-NONE X-NONE 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
📊
Key Findings & Data:Normal 0 21 false false false TR X-NONE X-NONE 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
💡
Conclusion & Impact:Normal 0 21 false false false TR X-NONE X-NONE 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
🔬Design:Article
📍Scope:Comprehensive Sample
⚙️Variables:Cyclohexyl isocyanide · dimedone · 3- cyclohexanedione

Abstract

Normal 0 21 false false false TR X-NONE X-NONE 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

🔖

Cite This Article

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, Volume: 23 Issue: 4. https://ajindex.com/articles/1269964

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (38)

  1. Dean, F.M., “Advances in Heterocyclic Chemistry”; Katritzky, A.R., Ed.; Academic; New York; 30: 167-238 (1982)
  2. Nakanishi, K., “Natural Products Chemistry”; Kodansha; Tokyo, (1974).
  3. Strenbach, D.D., Rossana, D.M.,”Intramolecular diels-alder reactions of the furan diene: substituent and solvent effects“, Tetrahedron Lett., 23: 303(1982).
  4. 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).
  5. Best, W.M., Wege, D.,” Intramolecular diels-alder reactions of benzynes application to the total synthesis of mansonone E”, Tetrahedron Lett., 22: 4877 (1981).
  6. Zhu, J., Bienayme, H.,“ Multicomponent Reactions“, Wiely-VCH, Weinheim, (2005).
  7. Litvinov, V.P.,”Multicomponent cascade heterocyclisation as a promising route to targeted synthesis of polyfunctional pyridines“, Russ. Chem. Rev., 72: 69 (2003).
  8. Ugi, I., Dömling, A., Hörl, W.,”Multicomponent Reactions“, Endeavour., 18: 115 (1994).
  9. Tietze, L.F., Modi, A.,”Multicomponent domino reactions for the synthesis of biologically active natural products and drugs“, Med. Res. Rev., 20: 304 (2000).
  10. 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).
  11. Passerini, M.,”Passerini Reaction“, Gazz Chim. Ital., 52: 432 (1992).
  12. Cristau, P.; Vors, J. P.; Zhu., “Rapid synthesis of cyclopeptide alkaloid-like para-cyclophanes”, J. QSAR Comb. Sci., 25: 519 (2006).
  13. Ugi, I., Meyr, R., Fetzer, U., Steinbrückner, C., “Versuche mit Isonitrilen”, Angew.Chem., 71: 386 (1959).
  14. Ugi, I., Steinbrückner, C.,”Über ein neues Kondensations-Prinzip“, Angew. Chem., 72: 267 (1960).
  15. Murakami, M.,”New Catalyzed Three-Component Cycloadditions for the Synthesis of Eight- Membered Carbocycles“, Angew. Chem. Int. Ed. 42: 718 (2003).
  16. Bienayme, H., Hulme, C., Oddon, G., Schmitt, P.,”Maximizing synthetic efficiency: Multi- component transformations lead the way“, Chem.Eur. J., 6: 3321 (2000).
  17. Dömling, A.,”Recent advances in isocyanide- based multicomponent chemistry“, Curr. Opin. Chem. Biol., 6: 306 (2002).
  18. Hulme, C., Gore, V.,” “Multi-component
  19. Reactions: Emerging Chemistry in Drug Discovery”
  20. ‘From Xylocain to Crixivan’“, Curr. Med. Chem., 10: 51 (2003).
  21. Orru, R. V. A., De Greef, M.,”Recent Advances in Solution-Phase Multicomponent Methodology for the Synthesis of Heterocyclic Compounds“, Synthesis, 1471 (2003).
  22. Balme, G., Bossharth, E., Monteiro, N.,”Pd- Assisted Multicomponent Synthesis of Heterocycles“, Eur. J. Org.Chem. 21: 4101 (2003).
  23. 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).
  24. Dömling, A., Ugi, I.,”Multicomponent Reactions with Isocyanides“, Angew. Chem. Int. Ed. 39, 3168 (2000).
  25. Marcaccini, S., Torroba, T.,”The use of isocyanides in heterocyclic synthesis. A review“, Org. Prep. Proced. Int., 25: 141(1993).
  26. Ugi, I., Lohberger, S., Karl, R. “In Comprehensive Organic Synthesis;” Trost, B. M. Fleming, I., Eds.; Pergamon: New York,; 2 (4-6): 1083 (1993).
  27. 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]
  28. Heravi, M.M., Bakhtiari, K., Oskooie,
  29. H.A.,”Communication: KHSO Supported onto
  30. Bentonite, A Versatile Reagent for Aromatization
  31. of Hantzsch 1,4-Dihydropyridines“, J. Chin.
  32. Chem. Soc., 54, 579 (2007).
  33. 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).
  34. Dean, F.M., “Advances in Heterocyclic Chemistry”; Katritzky, A.R., Ed.; Academic; New York; 30: 167-238 (1982)
  35. Cristau, P.; Vors, J. P.; Zhu., “Rapid synthesis of cyclopeptide alkaloid-like para-cyclophanes”, J. QSAR Comb. Sci., 25: 519 (2006).
  36. Ugi, I., Meyr, R., Fetzer, U., Steinbrückner, C., “Versuche mit Isonitrilen”, Angew.Chem., 71: 386 (1959).
  37. Ugi, I., Lohberger, S., Karl, R. “In Comprehensive Organic Synthesis;” Trost, B. M. Fleming, I., Eds.; Pergamon: New York,; 2 (4-6): 1083 (1993).
  38. 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]