Startseite One-pot synthesis of acenaphtho[1,2-b]pyrroles in the presence of supported ionic liquid catalyst
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One-pot synthesis of acenaphtho[1,2-b]pyrroles in the presence of supported ionic liquid catalyst

  • Reza Sandaroos EMAIL logo , Mohammad Taghi Goldani EMAIL logo und Saman Damavandi
Veröffentlicht/Copyright: 1. August 2012

Abstract

Eleven new 8-[(alkyl or aryl)amino]-9-(alkyl or aryl)acenaphtho[1,2-b]pyrroles were synthesized by one-pot reaction of (acenaphthylen-1-yloxy)trimethylsilane, alkyl or aryl aldehyde, ammonium acetate, and aryl or alkyl isocyanide in refluxing DMF.


Corresponding authors: Reza Sandaroos and Mohammad Taghi Goldani, Department of Chemistry, Faculty of Science, University of Birjand, Birjand, Iran and Department of Chemistry, Islamic Azad University, Birjand Branch, Birjand, Iran

References

Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Maximizing synthetic efficiency: multi-component transformations lead the way. Chem. Eur. J. 2000, 6, 3321–3329.10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO;2-ASuche in Google Scholar

Chrobok, A.; Baj, S.; Pudło, W.; Jarzebski, A. Supported hydrogensulfate ionic liquid catalysis in Baeyer-Villiger reaction. Appl. Catal. A: Gen. 2009, 366, 22–28.10.1016/j.apcata.2009.06.040Suche in Google Scholar

Firouzabadi, H.; Mohammadpoor-Baltork, I.; Kolagar, S. A rapid, selective, and efficient method for deprotection of silyl ethers catalyzed by bismuth(III) salts. Synth. Commun. 2001, 31, 905–909.10.1081/SCC-100103326Suche in Google Scholar

Fischer, J.; Hölderich, W. F. Baeyer-Villiger oxidation of cyclopentanone with aqueous hydrogen peroxide by acid heterogeneous catalysis. Appl. Catal. A: Gen. 1999, 180, 435–443.10.1016/S0926-860X(98)00378-0Suche in Google Scholar

González-Núñez, M. E.; Mello, R.; Olmos, A.; Asensio, G. Baeyer-Villiger oxidation with potassium peroxomonosulfate supported on acidic silica gel. J. Org. Chem. 2005, 70, 10879–10882.10.1021/jo051614vSuche in Google Scholar

González-Núñez, M. E.; Mello, R.; Olmos, A.; Asensio, G. Baeyer-Villiger oxidation in supercritical CO2 with potassium peroxomonosulfate supported on acidic silica gel. J. Org. Chem. 2006, 71, 6432–6436.10.1021/jo060753pSuche in Google Scholar

Heravi, M. M.; Baghernejad, B.; Oskooie, H. A.; Hekmatshoar, R. A novel and facile synthesis of 2-(cyclohexylamino)-6,7-dihydro-3-aryl-1H-indole-4(5H)-ones via a one-pot multi-component reaction. Tetrahedron Lett. 2008, 49, 6101–6103.10.1016/j.tetlet.2008.08.012Suche in Google Scholar

Manjula, A.; Rao, B. V.; Neelakantan, P. An inexpensive protocol for Biginelli reaction. Synth. Commun. 2004, 34, 2665–2671.10.1081/SCC-200025633Suche in Google Scholar

Mashraqui, S. H.; Karnik, M. A. Bismuth nitrate pentahydrate: a convenient reagent for the oxidation of Hantzch 1,4-dihydropyridines. Synthesis 1998, 713–714.10.1055/s-1998-4516Suche in Google Scholar

Mohammadpoor-Baltork, I.; Khosropour, A. R. Bismuth(III) salts as new catalyst for the selective conversion of trimethylsilyl and tetrahydropyranyl ethers to their corresponding acetates and formats. Synth. Commun. 2002, 32, 2433–2439.10.1081/SCC-120006016Suche in Google Scholar

Orru, A. Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds. Synthesis 2003, 1471–1499.10.1055/s-2003-40507Suche in Google Scholar

Passerini, M. Natural product synthesis using multicomponent reaction strategies. Gazz. Chim. Ital. 1921, 52, 432–435.Suche in Google Scholar

Qiao, K.; Hagiwara, H.; Yokoyama, C. Acidic ionic liquid modified silica gel as novel solid catalysts for esterification and nitration reactions. J. Mol. Catal. A: Chem. 2006, 246, 65–69.10.1016/j.molcata.2005.07.031Suche in Google Scholar

Schneekloth, J. S., Jr.; Kim, J.; Sorensen, E. J. An interrupted Ugi reaction enables the preparation of substituted indoxyls and aminoindoles. Tetrahedron 2009, 65, 3096–3101.10.1016/j.tet.2008.08.055Suche in Google Scholar PubMed PubMed Central

Song, J. J.; Tan, Z.; Reeves, J. T.; Fandrick, D. R.; Yee, N. K.; Senanayake C. H. N-heterocyclic carbene-catalyzed silyl enol ether formation. Org. Lett. 2008, 10, 877–880.10.1021/ol703025bSuche in Google Scholar PubMed

Strecker, M. The artificial synthesis of lactic acid and new homologous glycine. Liebigs Ann. Chem. 1850, 75, 27–45.10.1002/jlac.18500750103Suche in Google Scholar

Sugimura, R.; Qiao, K.; Tomida, D.; Yokoyama, C. Immobilization of acidic ionic liquids by copolymerization with styrene and their catalytic use for acetal formation. Catal. Commun. 2007, 8, 770–772.10.1016/j.catcom.2006.08.049Suche in Google Scholar

Sun, C.; Ji, S. J.; Liu, Y. J. ChemInform Abstract: A novel InCl3/SiO2-catalyzed hydroarylation of arenes with styrenes under solvent-free conditions. Chin. Chem. Soc. 2008, 55, 292–296.10.1002/chin.200836090Suche in Google Scholar

Sundberg, R. J. Indoles; Academic Press: London, 1996.Suche in Google Scholar

Trost, B. M. The atom economy – a search for synthetic efficiency. Science 1991, 254, 1471–1477.10.1126/science.1962206Suche in Google Scholar PubMed

Umkehrer, M.; Ross, G.; Jager, N.; Burdack, C.; Kolb, J.; Hu, H.; Alvim-Gaston, M.; Hulme, C. Diversity oriented synthesis of benzoxazoles and benzothiazoles. Tetrahedron Lett. 2007, 48, 2213–2216.10.1016/j.tetlet.2007.01.061Suche in Google Scholar

Von Wangelin, A. J.; Neumann, H.; Gördes, D.; Klaus, S.; Strübing, D.; Beller, M. Multicomponent coupling reactions for organic synthesis: chemoselective reactions with amide-aldehyde mixtures. Chem. Eur. J. 2003, 9, 4286–4294.10.1002/chem.200305048Suche in Google Scholar PubMed

Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis, 2nd edition; Wiley-VCH: Weinheim, 2007.10.1002/9783527621194Suche in Google Scholar

Yadav, J. S.; Reddy, B. V. S.; Sridhar, P.; Reddy, J. S. S.; Nagaiah, K.; Lingaiah, N. Green protocol for the Biginelli three-component reaction: Ag3PW12O40 as a novel, water-tolerant heteropoly acid for the synthesis of 3,4-dihydropyrimidinones. Eur. J. Org. Chem. 2004, 3, 552–557.10.1002/ejoc.200300559Suche in Google Scholar

Received: 2011-12-20
Accepted: 2012-06-25
Published Online: 2012-08-01
Published in Print: 2012-08-01

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Heruntergeladen am 22.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/hc-2011-0126/html
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