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Synthesis 2011(9): 1489-1493
DOI: 10.1055/s-0030-1259990
DOI: 10.1055/s-0030-1259990
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
An Efficient Synthesis of Pyrrolocoumarins and Pyrroloquinolones by Acid-Catalysed Cyclisation of Acetylenic Amines in Water
Further Information
Received
15 December 2010
Publication Date:
04 April 2011 (online)
Publication History
Publication Date:
04 April 2011 (online)
Abstract
A simple H+-catalysed cyclisation of acetylenic amines for the synthesis of pyrrolocoumarins and pyrroloquinolones under conventional heating or microwave irradiation has been achieved. The reaction requires inexpensive catalyst and simple yet clean reaction conditions and offers potentially bioactive heterocycles in 82-95% yields.
Key words
pyrrolocoumarin - pyrroloquinolone - Brønsted acid catalysis - intramolecular cyclisation - microwave irradiation
- 1
Watanabe M.Sato T.Inomata H.Smith RL.Arai K.Kruse A.Dinjus E. Chem. Rev. 2004, 104: 5803 - 2
Dallinger D.Kappe CO. Chem. Rev. 2007, 107: 2563 - 3 For an introduction to the use
of organometallic catalysts in aqueous phase catalysis, see:
Aqueous-Phase Organometallic Catalysis, Concepts and Applications
Cornils B.Herrmann WA. Wiley-VCH; Weinheim: 1998. -
4a
Chen L.Li CJ. Org. Lett. 2004, 6: 3151 -
4b
Li CJ. Chem. Rev. 1993, 93: 2023 - 5
Siskin K.Katritzky AR. Science 1991, 254: 231 - 6
Strauss CR.Trainor RW. Aust. J. Chem. 1995, 48: 1665 -
7a
Baudel V.Cazier F.Woisel P.Surpateanu G. Eur. Polymer. J. 2002, 38: 615 -
7b
An JY.Bagnell L.Cablewski T.Strauss CR.Trainor RW. J. Org. Chem. 1997, 62: 2505 - For recent reviews on the use of microwaves in organic synthesis, see:
-
8a
Larhed M.Moberg C.Hallberg A. Acc. Chem. Res. 2002, 35: 712 -
8b
Lew A.Krutzik PO.Hart ME.Chamberlin AR. J. Comb. Chem. 2002, 4: 95 -
8c
Linström P.Tierney J.Wathey B.Westman J. Tetrahedron 2001, 57: 9225 -
8d
Perreux L.Loupy A. Tetrahedron 2001, 57: 9199 -
8e
Deshayes S.Liagre M.Loupy A.Luche J.-L.Petit A. Tetrahedron 1999, 55: 10851 - 9
Katritzky AR.Siskin M. Chem. Rev. 2001, 101: 837 - 10
Polshettiwar V.Rajender SV. Chem. Soc. Rev. 2008, 37: 1546 - 11
Polshettiwar V.Rajender SV. Acc. Chem. Res. 2008, 41: 629 - 12
Wei WC.Keh CK.Li C.-J.Varma ES. Clean Technol. Environ. Policy 2004, 7: 62 -
13a
Jones RA.Bean GP. The Chemistry of Pyrroles Academic; London: 1977. p.1-5 -
13b
Sundberg RJ. In Comprehensive Heterocyclic Chemistry Vol. 4:Katritzky AR.Rees CW. Pergamon; Oxford: 1984. p.370-376 -
13c
Sundberg RJ. In Comprehensive Heterocyclic Chemistry II Vol. 2:Katritzky AR.Rees CW. Pergamon; Oxford: 1996. p.119-206 -
13d
Boger DL.Boyce CW.Labrili MA.Sehon CA.Jin Q. J. Am. Chem. Soc. 1999, 121: 54 ; and references cited therein - 14
The
Chemistry of Heterocyclic Compounds
Parts 1 and
2:
Jones RA. Wiley; Toronto: 1990. -
15a
Tietze LF.Nordmann G. Synlett 2001, 337 -
15b
Groenendaal L.Meijer E.-W.Vekemans JAJM. In Electronic Materials: The Oligomer ApproachMüllen K.Wegner G. Wiley-VCH; Weinheim: 1997. - 16
Boyd DR.Sharma ND.Barr SA.Carroll JG.Mackerracher D.Malone JF. J. Chem. Soc., Perkin Trans. 1 2000, 3397 - 17
Bar G.Parsons AF.Thomas CB. Tetrahedron 2001, 57: 4719 - 18
Lee YR.Kim BS.Kweon HI. Tetrahedron 2000, 56: 3867 - 19
Pirrung MC.Blume F. J. Org. Chem. 1999, 64: 3642 - 20
Dickinson JM. Nat. Prod. Rep. 1993, 10: 71 - 21
Hiremath SP.Badiger GR.Jivanagi AS.Purohit MG. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1992, 31: 583 -
22a
Majumdar KC.Mondal S. Tetrahedron Lett. 2008, 49: 2418 -
22b
Majumdar KC.Chattopadhyay B.Samanta S. Synthesis 2009, 311 -
22c
Majumdar KC.Chakravorty S.Shyam PK.Taher A. Synthesis 2009, 403 -
22d
Majumdar KC.Samanta S.Nandi RK.Chattopadhyay B. Tetrahedron Lett. 2010, 51: 3807 -
22e
Majumdar KC.De N.Roy B. Synthesis 2010, 4207 -
23a
Majumdar KC.Taher A.Ponra S. Tetrahedron Lett. 2010, 51: 2297 -
23b
Majumdar KC.Taher A.Ponra S. Tetrahedron Lett. 2010, 51: 147 -
23c
Majumdar KC.Taher A.Ponra S. Synthesis 2010, 4307 - 24
Koradin C.Dohle W.Rodriguez AL.Schmidt B.Knochel P. Tetrahedron 2003, 59: 1571 - 25
Zhang Y.Donahue JP.Li CJ. Org. Lett. 2007, 9: 627 - 26
Trost BM.McClory A. Angew. Chem. Int. Ed. 2007, 46: 2074 - 27
Knight DW.Sharland CM. Synlett 2003, 2258