Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 10
263
Views
11
CrossRef citations to date
0
Altmetric
Original Articles

One-pot multicomponent diastereoselective synthesis of novel dihydro-1H-furo[2,3-c]pyrazoles

, , &
Pages 878-884 | Received 27 Jan 2016, Published online: 24 May 2016

References

  • (a) Schreiber, S. L. Diversity oriented synthesis: A challenge for synthetic chemists. Science 2000, 287, 1964–1969; (b) Trost, B. M. Atom economy: A challenge for organic synthesis. Angew. Chem., Int. Ed. Engl. 1995, 34, 259–281; (c) Tietze, L. F. Domino reactions in organic synthesis. Chem. Rev. 1996, 96, 115–136; (d) Ugi, I. Recent progress in the chemistry of multicomponent reactions. Pure Appl. Chem. 2001, 73, 187–191; (e) Dömling, A. Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem. Rev. 2006, 106, 17–89; (f) Timmons, C.; Kattuboina, A.; Banerjee, S.; Li, G. Tetrahedron 2006, 62, 7151.
  • (a) Ramon, D. J.; Yus, M. Asymmetric multicomponent reactions (AMCRs): The new frontier. Angew. Chem. Int. Ed. 2005, 44, 1602–1634; (b) Dömling, A.; Ugi, I. Multicomponent reactions with isocyanides. Angew. Chem. Int. Ed. 2000, 39, 3168–3172; (c) Zhu, J.; Bienayme, H. In Multicomponent Reactions, Wiley: Weinheim, Germany, 2005.
  • (a) Sunderhaus, J. D.; Dockendorff, C.; Martin, S. F. Applications of multicomponent reactions for the synthesis of diverse heterocyclic scaffolds. Org. Lett. 2007, 9, 4223–4228; (b) Muller, F. L.; Constantieux, T.; Rodriguez, J. Multicomponent domino reaction from β-ketoamides: Highly efficient access to original polyfunctionalized 2,6-diazabicyclo[2.2.2]octane cores. J. Am. Chem. Soc. 2005, 127, 171–176; (c) Haurena, C.; Gall, E. L.; Sengmany, S.; Martens, T.; Troupel, M. A. Straightforward three-component synthesis of α-amino esters containing a phenylalanine or a phenylglycine scaffold. J. Org. Chem. 2010, 75, 2645–2650; (d) Willy, B.; Muller, T. J. J. Regioselective three-component synthesis of highly fluorescent 1,3,5-trisubstituted pyrazoles. Eur. J. Org. Chem. 2008, 4157–4168.
  • (a) Pal, D.; Saha, S.; Singh, S. Importance of pyrazole moiety in the field of cancer. Int. J. Pharm. Pharm. Sci. 2012, 4, 98–104; (b) Secci, D.; Bolasco, A.; Chimenti, P.; Carradori, S. The state of the art of pyrazole derivatives as monoamine oxidase inhibitors and antidepressant/anticonvulsant agents. Curr. Med. Chem. 2011, 18, 5114–5144; (c) Bekhit, A. A.; Hymete, A.; Bekhit, A. E.-D. A.; Damtew, A.; Aboul-Enein, H. Y. Pyrazoles as promising scaffold for the synthesis of anti-inflammatory and/or antimicrobial agent: A review. Mini-Rev. Med. Chem. 2010, 10, 1014–1033; (d) Kumar, S.; Bawa, S.; Drabu, S.; Kumar, R.; Gupta, H. Biological activities of pyrazoline derivatives: A recent development. Rec. Patents Anti-Infect. Drug Discov. 2009, 4, 154–163; (f) Lamberth, C. Pyrazole chemistry in crop protection. Heterocycles 2007, 71, 1467; (g) Mukherjee, R. Coordination chemistry with pyrazole-based chelating ligands: Molecular structural aspects. Coord. Chem. Rev. 2000, 203, 151–218.
  • (a) Lees, P.; Higgins, A. J. Clinical pharmacology in therapeutic uses of non-steroidal anti-inflammatory drugs in the horse. Equine Vet. J. 1985, 17, 83–96; (b) Singh, N.; Jabeen, T.; Somvanshi, R. K.; Sharma, S.; Dey, S.; Singh, T. P. Phospholipase A2 as a target protein for nonsteroidal anti-inflammatory drugs (NSAIDs): Crystal structure of the complex formed between phospholipase A2 and oxyphenbutazone at 1.6 Å resolution. Biochemistry 2004, 43, 14577–14583; (c) Manna, F.; Chimenti, F.; Bolasco, A.; Cenicola, M. L.; D’Amico, M.; Parrillo, C.; Rossi, F.; Marmo, E. Anti-inflammatory, analgesic and antipyretic N-acetyl-Δ2-pyrazolines and dihydrothienocoumarines. Eur. J. Med. Chem. 1992, 30, 633–639.
  • Li-Chen, C.; Li-Jiau, H.; Jai-Sing, Y.; Fang-Yu, L.; Che-Ming, T.; Sheng-Chu, K. Synthesis of 1-benzyl-3-(5′-hydroxymethyl-2′-furyl)indazole analogues as novel antiplatelet agents. Bioorg. Med. Chem. Lett. 2007, 15, 1732–1740.
  • Chou, L. C.; Huang, L. J.; Yang, J. S.; Lee, F. Y.; Teng, C. M.; Kuo, S. C. Synthesis of furopyrazole analogs of 1-benzyl-3-(5-hydroxymethyl-2-furyl)indazole (YC-1) as novel anti-leukemia agents. Bioorg. Med. Chem. 2007, 15, 1732–1740.
  • (a) Samir, B.; Wesam, K.; Ahmed, A. F. Synthesis and antimicrobial activity of some new 4-hetarylpyrazole and furo[2,3-c]pyrazole derivatives. Eur. J. Med. Chem, 2011, 46, 2555–2561; (b) Gianluigi, B.; Luisa, G.; Giorgio, M.; Gaetano, Z. The first case of asymmetric induction in intramolecular nitrile imine cycloadditions: Synthesis of enantiopure 3-substituted 6-oxo-2,3,3a,5-tetrahydro-4-carbomethoxy-furo[3,4-c]pyrazoles. Tetrahedron: Asymmetry 1999, 10, 487–492; (c) Lara, D.; Benassuti, L. G.; Giorgio, M. Stereoselective intramolecular cycloadditions of homochiral nitrilimines: Synthesis of enantiopure (6S)-substituted-2,3,3a,4,5,6-hexahydro-furo[3,4-c]pyrazoles. Tetrahedron: Asymmetry 2004, 15, 1127–1131; (d) Ibrahim, M. A. A. Studies in Vilsmeier–Haack reaction, IX: Synthesis and application of novel heterocyclo-substituted furo[2,3-c:5,4-c′]dipyrazole derivatives. Bull. Chem. Soc. Jpn. 1992, 65, 1652–1656.
  • Hoz, A.; Ortiz, A. D.; Moreno, A. Chem. Soc. Rev. 2005, 34, 164.
  • (a) Rao, H. S. P.; Swamy, T. V. Synthesis of 3-aroylcoumarin-flavone hybrids. Lett. Org. Chem. 2012, 9, 218–220; (b) Rao, H. S. P.; Swamy, T. V. Synthesis of spirobiindane-based bis-flavanones and bis-chroman-4-ones by Kabbe reaction. Lett. Org. Chem. 2013, 10, 307–310; (c) Rao, H. S. P.; Swamy, T. V. Synthesis and photochromic properties of spirobiindane-based bis-coumarin. Proc. Natl. Acad. Sci., India, Sect. A Phys. Sci. 2015, 85, 41–49.
  • Rao, H. S. P.; Swamy, T. V. Synthesis and transformations of 4H-chromene 4-hydroxy-2H-pyran-2-one and 4H-chromene 4-hydroxycoumarin conjugates. J. Chem. Sci. 2013, 125, 777–790.

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.