RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2012; 44(13): 2079-2083
DOI: 10.1055/s-0031-1291161
DOI: 10.1055/s-0031-1291161
paper
Montmorillonite K-10 Catalyzed, Microwave-Assisted Cyclization of Acetylenic Amines: An Efficient Synthesis of Pyrrolocoumarins and Pyrroloquinolones
Weitere Informationen
Publikationsverlauf
Received: 22. Februar 2012
Accepted after revision: 24. April 2012
Publikationsdatum:
31. Mai 2012 (online)
Abstract
A microwave-assisted montmorillonite K-10 catalyzed synthesis of pyrrolocoumarins and pyrroloquinolones from acetylenic amine is described. The reaction utilizes montmorillonite K-10 as an inexpensive, recyclable, and environmentally benign acid catalyst. Reactions were completed in few minutes under microwave irradiation and provided excellent yields. The efficient and eco-friendly catalyst and the convenience of the product isolation make the process an attractive alternative for the synthesis of these important heterocycles.
Key words
microwave irradiation - montmorillonite K-10 - acetylenic amine - pyrrolocoumarin - pyrroloquinoloneSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Jones RA, Bean GP. The Chemistry of Pyrroles . Academic; London: 1977: 1
- 1b Sundberg RJ In Comprehensive Heterocyclic Chemistry . Vol. 4. Katritzky AR, Rees CW. Pergamon; Oxford: 1984: 370
- 1c Sundberg RJ In Comprehensive Heterocyclic Chemistry II . Vol. 2. Katritzky AR, Rees CW, Scriven EF. V. Pergamon; Oxford: 1996: 149
- 1d Boger DL, Boyce CW, Labrili MA, Sehon CA, Jin Q. J. Am. Chem. Soc. 1999; 121: 54 ; and references cited therein
- 2 The Chemistry of Heterocyclic Compounds . Vol. 48, Parts 1 and 2. Jones RA. Wiley; New York: 1990
- 3a Tietze LF, Nordmann G. Synlett 2001; 337
- 3b Groenendaal L, Meijer E.-W, Vekemans JA. J. M In Electronic Materials: The Oligomer Approach . Müllen K, Wegner G. Wiley-VCH; Weinheim: 1997
- 4 Boyd DR, Sharma ND, Barr SA, Carroll JG, Mackerracher D, Malone JF. J. Chem. Soc., Perkin Trans. 1 2000; 3397
- 5 Bar G, Parsons AF, Thomas CB. Tetrahedron 2001; 57: 4719
- 6 Lee YR, Kim BS, Kweon HI. Tetrahedron 2000; 56: 3867
- 7 Pirrung MC, Blume F. J. Org. Chem. 1999; 64: 3642
- 8 Dickinson JM. Nat. Prod. Rep. 1993; 10: 71
- 9a Rodighiero P, Chilin A, Pastorini G, Guiotto A. J. Heterocycl. Chem. 1987; 24: 1041
- 9b Guiotto A, Chilin A, Manzini P, Dall’Acqua F, Bordin F, Rodighiero P. Farmaco 1995; 50: 479
- 10 Gia O, Mobilio S, Chilin A, Rodghiero P, Palumbo M. J. Photochem. Photobiol., B. 1988; 2: 435
- 11 Quanten E, Adriaens P, Schryver FC, Roelandts R, Degreef H. Photochem. Photobiol. 1986; 43: 485
- 12 Kontogiorgis C, Litinas KE, Makri A, Nicolaides DN, Vronteli A, Litina DJ. H, Pontiki E, Siohou A. J. Enzyme Inhib. Med. Chem. 2008; 23: 43
- 13 Chen L, Hu T.-S, Yao z.-J. Eur. J. Org. Chem. 2008; 6175
- 14a Gates BC. Catalysis by Solid Acids . In Encyclopedia of Catalysis . Vol. 2. Horváth I. Wiley; New York: 2003: 104
- 14b Molnár Á. Curr. Org. Chem. 2008; 12: 159
- 14c Polshettiwar V, Varma RS. Acc. Chem. Res. 2008; 41: 629
- 14d Dasgupta S, Török B. Curr. Org. Synth. 2008; 5: 321
- 14e Loupy A. Microwaves in Organic Synthesis. Wiley-VCH; Weinheim: 2005
- 14f Kappe CO, Stadler A. Microwaves in Organic and Medicinal Chemistry. Wiley-VCH; Weinheim: 2005
- 14g Kappe CO, Dallinger D. Nat. Rev. 2006; 5: 51
- 15a Augustine RL. Heterogeneous Catalysis for the Synthetic Chemists. Marcel Dekker; New York: 1996
- 15b Smith GV, Notheisz F. Heterogeneous Catalysis in Organic Chemistry. Academic Press; San Diego: 1999
- 16a Benesi HA, Winquest BH. C. Adv. Catal. 1978; 27: 97
- 16b Vaccari A. Appl. Clay Sci. 1999; 14: 161
- 16c Nikalje MD, Phukan P, Sudalai A. Org. Prep. Proced. Int. 2000; 32: 1
- 16d Varma RS. Tetrahedron 2002; 58: 1235
- 16e Dasgupta S, Török B. Org. Prep. Proced. Int. 2008; 40: 1
- 17a Varma RS, Saini RK. Synlett 1997; 857
- 17b Varma RS, Kumar D. Tetrahedron Lett. 1999; 40: 7665
- 17c Vass A, Dudas J, Varma RS. Tetrahedron Lett. 1999; 40: 4951
- 18a Abid M, De Paolis O, Török B. Synlett 2008; 410
- 18b Landge SM, Berryman M, Török B. Tetrahedron Lett. 2008; 49: 4505
- 18c Landge SM, Schmidt A, Outerbridge V, Török B. Synlett 2007; 1600
- 19a Majumdar KC, Taher A, Ponra S. Tetrahedron Lett. 2010; 51: 2297
- 19b Majumdar KC, Taher A, Ponra S. Tetrahedron Lett. 2010; 51: 147
- 19c Majumdar KC, Taher A, Ponra S. Synlett 2010; 735
- 19d Majumdar KC, Ray K, Ponra S. Tetrahedron Lett. 2010; 51: 5437
- 19e Majumdar KC, Taher A, Ponra S. Synthesis 2010; 4043
- 19f Majumdar KC, Ponra S, Ganai S. Synlett 2010; 2575
- 19g Majumdar KC, Ponra S, Ghosh D, Taher A. Synlett 2011; 104
- 19h Majumdar KC, Ponra S, Ghosh D. Synthesis 2011; 1132
- 19i Majumdar KC, Ponra S, Nandi RK. Eur. J. Org. Chem. 2011; 6909
- 20a Mei De-S, Qu Y, He J-X, Chen L, Yao Z-J. Tetrahedron 2011; 67: 2251
- 20b Mentel M, Peters M, Albering J, Breinbauer R. Tetrahedron 2011; 67: 965
- 20c Chen L, Xu M-H. Adv. Synth. Catal. 2009; 351: 2005
- 20d Suslov VV, Gordeev EN, Traven VF. Chem. Heterocycl. Compd. 2004; 40: 1315
- 20e Jiang W, Alford VC, Qiu Y, Bhattacharjee S, John TM, Haynes-Johnson D, Kraft PJ, Lundeen SG, Sui Z. Bioorg. Med. Chem. 2004; 12: 1505
- 20f Gonzalez JC, Lobo-Antunes J, Perez-Lourido P, Santana L, Uriarte E. Synthesis 2002; 475
- 20g Traven VF, Suslov VV, Gordeev EN. ARKIVOC 2000; (iv): 603
- 20h Dumas C, Kan-Fan C, Carniaux J-F, Royer J, Husson H-P. Tetrahedron Lett. 1999; 40: 8211
- 20i Fujihara M, Kawazu M. Chem. Pharm. Bull. 1972; 20: 88
- 21a Majumdar KC, Mondal S. Tetrahedron Lett. 2008; 49: 2418
- 21b Majumdar KC, Chattopadhyay B, Samanta S. Synthesis 2009; 311
- 21c Majumdar KC, Chakravorty S, Shyam KP, Taher A. Synthesis 2009; 403
- 21d Majumdar KC, Samanta S, Nandi RK, Chattopadhyay B. Tetrahedron Lett. 2010; 51: 3807
- 21e Majumdar KC, De N, Roy B. Synthesis 2010; 4207
- 21f Majumdar KC, Ponra S, Hazra S, Roy B. Synthesis 2011; 1489