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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 18
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Articles

A one-pot three-component synthesis of fused Spiro-Indoline/Indene derivatives derived from ethynyl azaindole by 1,3-dipolar cycloaddition reaction

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Pages 2441-2451 | Received 10 May 2018, Published online: 08 Oct 2018

References

  • Kawasaki, T.; Higuchi, K. Simple Indole Alkaloids and Those with a Nonrearranged Monoterpinoid Unit. Nat. Prod. Rep. 2005, 22, 761–793. DOI: 10.1039/B502162F.
  • Kim, W. G.; Kim, J. P.; Koshino, H.; Shin-Ya, K.; Seto, H.; Yoo, I. D. Benzastatins E, F, and g: New Indoline Alkaloids with Neuronal Cell Protecting Activity from Streptomyces nitrosporeus. Tetrahedron 1997, 53, 4309–4316. DOI: 10.1016/S0040-4020(97)00157-9.
  • Matsuoka, H.; Kato, N.; Ohi, N.; Miyamoto, K.; Mihara, M.; Takeda, Y. Antirheumatic Agents. III. Novel Methotrexate Derivatives Bearing an Indoline Ring and a Modified Ornithine or Glutamic Acid. Chem. Pharm. Bull. 1997, 45, 1146–1150. DOI: 10.1248/cpb.45.1146.
  • Nefzi, A.; Ostresh, J. M.; Houghten, R. A. The Current Status of Heterocyclic Combinatorial Libraries. Chem. Rev. 1997, 97, 449–472. DOI: 10.1021/cr960010b.
  • Thompson, L. A. Recent Applications of Polymer-Supported Reagents and Scavengers in Combinatorial, Parallel, or Multistep Synthesis. Curr. Opin. Chem. Biol 2000, 4, 324–337. DOI: 10.1016/S1367-5931(00)00096-X.
  • Balme, G.; Bossharth, E.; Monteiro, N. Pd‐Assisted Multicomponent Synthesis of Heterocycles. Eur. J. Org. Chem. 2003, 2003, 4101–4111. DOI: 10.1002/ejoc.200300378.
  • Nicolaou, K. C.; Roecker, A. J.; Hughes, R.; Van Summeren, R.; Pfefferkorn, J. A.; Winssinger, N. Novel Strategies for the Solid Phase Synthesis of Substituted Indolines and Indoles. Bioorg. Med. Chem. 2003, 11, 465–476. DOI: 10.1021/ja994373f.
  • Nicolaou, K. C.; Roecker, A. J.; Pfefferkorn, J. A.; Cao, G. Q. A Novel Strategy for the Solid-Phase Synthesis of Substituted Indulines. J. Am. Chem. Soc. 2000, 122, 2966–2967. DOI: 10.1021/ja994373f.
  • Bytschkov, I.; Siebeneicher, H.; Doye, S. A Flexible Synthesis of Indoline, Indolizidine, and Pyrrolizidine Derivatives. Eur. J. Org. Chem. 2003, 2003, 2888–2902. DOI: 10.1002/ejoc.200300123.
  • Adams, N. D.; Adams, J. L.; Burgess, J. L.; Chaudhari, A. M.; Copeland, R. A.; Donatelli, C. A.; Drewry, D. H.; Fisher, K. E.; Hamajima, T.; Hardwicke, M. A.; et al. Discovery of GSK 1070916, a Potent and Selective Inhibitor of Aurora B/C Kinase. J. Med. Chem. 2010, 53, 3973–4001. DOI: 10.1021/jm901870q.
  • Dandia, A.; Jain, A. K.; Laxkar, A. K.; Bhati, D. S. A Highly Efficient Protocol for the Regio and Stereoselective Synthesis of Spiro Pyrrolidine and Pyrrolizidine Derivatives by Multicomponent Reaction. Tetrahedron Letters 2013, 54, 3180–3184. DOI: 10.1016/j.tetlet.2013.04.033.
  • Grigg, R.; Thornton-Pett, M.; Yoganathan, G. Sequential 1,3-Dipolar Cycloaddition-Pictet-Spengler Spirocyclisation Reactions of Metallo-Azomethine Ylides from Aliphatic Aldimines. Tetrahedron 1999, 55, 8129–8140. DOI: 10.1016/S0040-4020(99)00420-2.
  • Dondas, H. A.; Duraisingham, J.; Grigg, R.; MacLachlan, W. S.; MacPherson, D. T.; Thornton-Pett, M.; Sridharan, V.; Suganthan, S. Cycloaddition Pictet–Spengler Reactions. A Versatile Tactical Combination. Tetrahedron 2000, 56, 4063–4070. DOI: 10.1016/S0040-4020(00)00320-3.
  • Chavre, S. N.; Choo, H.; Lee, J. K.; Pae, A. N.; Kim, Y.; Cho, Y. S. Exocyclic Products, Cis-2,3,5-Trisubstituted Tetrahydrofurans, and Cis-2,3,6-Trisubstituted Tetrahydropyrans via Prins-Type Cyclization. J. Org. Chem. 2008, 73, 7467–7471. DOI: 10.1021/jo800967p.
  • Vedejs, E.; Piotrowski, D. W.; Tucci, F. C. Oxazolium-Derived Azomethine Ylides. External Oxazole Activation and Internal Dipole Trapping in the Synthesis of an Aziridinomitosene. J. Org. Chem. 2000, 65, 5498–5505. DOI: 10.1021/jo0001277.
  • Pandey, G.; Sahoo, A. K.; Bagul, T. D. [3. + 2]-Cycloaddition of Nonstabilized Azomethine Ylides. 10. An Efficient Strategy for the Construction of x-Azatricyclo [m.n.0.0a, b] Alkanes by Intramolecular Cycloaddition of Cyclic Azomethine Ylide. Org. Lett. 2000, 2, 2299–2301. DOI: 10.1021/ol006070s.
  • Vedejs, E.; Klapars, A.; Naidu, B. N.; Piotrowski, D. W.; Tucci, F. C. Enantiocontrolled Synthesis of (1S,2S)-6-Desmethyl-(Methylaziridino) Mitosene. J. Am. Chem. Soc. 2000, 122, 5401–5402. DOI: 10.1021/ja994504c.
  • Coldham, I.; Crapnell, K. M.; Moseley, J. D.; Rabot, R. Intramolecular Azomethine Ylide Cycloaddition Reactions to Give Octahydroindoles. J. Chem. Soc, Perkin Trans. 1 2001, 15, 1758–1763. DOI: 10.1039/B104390K.
  • Novikov, M. S.; Khlebnikov, A. F.; Besedina, O. V.; Kostikov, R. R. First Example of Intramolecular Cycloaddition of Carbene-Derived Azomethine Ylides in a Domino Reaction of Difluorocarbene with Schiff Bases. Tetrahedron Lett. 2001, 32, no–535. DOI: 10.1002/chin.200115138.
  • Narayanarao, M.; Koodlur, L.; Revanasiddappa, V. G.; Gopal, S.; Kamila, S. Multicomponent Synthesis of Spiropyrrolidine Analogues Derived from Vinylindole/Indazole by a 1,3-Dipolar Cycloaddition Reaction. Beilstein J. Org. Chem. 2016, 12, 2893–2897. DOI: 10.3762/bjoc.12.288.
  • Gehringer, M.; Forster, M.; Laufer, S. A. Solution-Phase Parallel Synthesis of Ruxolitinib-Derived Janus Kinase Inhibitors via Copper-Catalyzed Azide–Alkyne Cycloaddition. ACS Comb. Sci. 2015, 17, 5–10. DOI: 10.1021/co500122h.
  • Ramgren, S. D.; Garg, N. K. Palladium-Catalyzed Acetylation of Arenes. Org. Lett. 2014, 16, 824–827. DOI: 10.1021/ol403570z.
  • Khoje, A. D.; Charnock, C.; Wan, B.; Franzblau, S.; Gundersen, L. L. Synthesis and Antimycobacterial Activities of Non-Purine Analogs of 6-Aryl-9-Benzylpurines: Imidazopyridines, Pyrrolopyridines, Benzimidazoles, and Indoles. Bioorg. Med. Chem 2011, 19, 3483–3491. DOI: 10.1016/j.bmc.2011.04.023.
  • Rao, J. N. S.; Raghunathan, R. An Expedient Diastereoselective Synthesis of Pyrrolidinyl Spirooxindoles Fused to Sugar Lactone via [3 + 2] Cycloaddition of Azomethine Ylides. Tetrahedron Lett. 2012, 53, 854–858. DOI: 10.1016/j.tetlet.2011.12.025.
  • Lakshmi, N. V.; Thirumurugan, P.; Perumal, P. T. An Expedient Approach for the Synthesis of Dispiropyrrolidine Bisoxindoles, Spiropyrrolidine Oxindoles and Spiroindane-1,3-Diones through 1,3-Dipolar Cycloaddition Reactions. Tetrahedron Lett. 2010, 51, 1064–1068. DOI: 10.1016/j.tetlet.2009.12.079.

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