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Synthesis 2010(18): 3179-3187
DOI: 10.1055/s-0030-1258180
DOI: 10.1055/s-0030-1258180
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Multicomponent Approach for the Synthesis of Phenanthridine and Acridine Ring Systems via the Coupling of Fischer Carbene Complexes with Heteroaromatic o-Alkynyl Carbonyl Derivatives
Further Information
Received
5 May 2010
Publication Date:
16 July 2010 (online)
Publication History
Publication Date:
16 July 2010 (online)
Abstract
A one-pot multicomponent synthesis of phenanthridine and acridine derivatives is described. This method includes the in situ generation of furo[3,4-c]isoquinoline and furo[3,4-b]quinoline intermediates by the coupling of heteroaromatic o-alkynyl carbonyl derivatives with Fischer carbene complexes and subsequent trapping of these intermediates by suitable dienophiles.
Key words
azaisobenzofuran - heterocycles - Diels-Alder reaction - chromium - carbene complexes
-
1a For
a review of phenanthridine synthesis, see:
Keller PA. In Science of Synthesis Vol. 15:StC. Black D. Georg Thieme; Stuttgart: 2005. Section 15.11. p.1065-1088 -
1b
Balasubramanian M.Keay JG. In Comprehensive Heterocyclic Chemistry II Vol. 5:McKillop AE.Katritzky AR.Rees CW.Scriven EFV. Elsevier; Oxford: 1996. p.245 - 2
Albert A. The Acridines 2nd ed.: Edward Arnold Ltd; London: 1966. - Some representative phenanthridine syntheses of this century include:
-
3a
Della Ca’ N.Motti E.Catellani M. Adv. Synth. Catal. 2008, 350: 2513 -
3b
Bowman WR.Lyon JE.Pritchard GJ. Synlett 2008, 2169 -
3c
Portela-Cubillo F.Scanlan EM.Scott JS.Walton JC. Chem. Commun. 2008, 4189 -
3d
Marsden SP.McGonagle AE.McKeever-Abbas B. Org. Lett. 2008, 10: 2589 -
3e
Donaldson LR.Haigh D.Hulme AN. Tetrahedron 2008, 64: 468 -
3f
Sripada L.Teske JA.Deiters A. Org. Biomol. Chem. 2008, 6: 263 -
3g
Pandey G.Balakrishnan M. J. Org. Chem. 2008, 73: 8128 -
3h
Buden ME.Rossi RA. Tetrahedron Lett. 2007, 48: 8739 -
3i
Ghorai BK.Duan S.Jiang D.Herndon JW. Synthesis 2006, 3661 -
3j
Shou W.-G.Yang Y.-Y.Wang Y.-G. J. Org. Chem. 2006, 71: 9241 -
3k
Kumemura T.Choshi T.Yukawa J.Hirose A.Nobuhiro J.Hibino S. Heterocycles 2005, 66: 87 -
3l
Ghorai BK.Jiang D.Herndon JW. Org. Lett. 2003, 5: 4261 -
4a
Sourdon V.Mazoyer S.Pique V.Galy J.-P. Molecules 2001, 6: 673 -
4b
Silva TG.Barbosa FSV.Brandao SSF.Lima MCA.Galdino SL.Pitta IR.Barbe J. Heterocycl. Commun. 2001, 7: 523 -
4c
Veverkova E.Noskova M.Toma S. Synth. Commun. 2002, 32: 729 -
4d
Suzuki H.Tanka Y. J. Org. Chem. 2001, 66: 2227 -
4e
Seijas JA.Vazquz-Tato MP.Martinez MM.Rodriguez-Parga J. Green Chem. 2002, 4: 390 -
4f
Goossens R.Smet M.Dehaen W. Tetrahedron Lett. 2002, 43: 6605 -
4g
Laursen BW.Krebs FC. Chem. Eur. J. 2001, 7: 1773 -
4h
Datta I.Das TK.Ghosh SN. Tetrahedron Lett. 1989, 30: 4009 - 5
Bienayme H.Hulme C.Oddon G.Schmitt P. Chem. Eur. J. 2000, 6: 3321 - 6
Jana GP.Ghorai BK. Lett. Org. Chem. 2009, 6: 372 - Isobenzofuran intermediates can be generated using Fischer carbene chemistry.
-
7a For the first example of
this reaction, see:
Jiang D.Herndon JW. Org. Lett. 2000, 2: 1267 -
7b For the latest examples
of this reaction, see:
Duan S.Sinha-Mahapatra DK.Herndon JW. Org. Lett. 2008, 10: 1541 - 8
Barbry D.Sokolowski G.Champagne P. Synth. Commun. 2002, 32: 1787 - 9
Rüger W.Konz E.Bartmann W. Synthesis 1988, 680 - 10
Jana GP.Ghorai BK. Tetrahedron 2007, 63: 12015 - 3-Formyl-2-iodoquinoline was prepared from 2-chloro-3-formylquinoline by a halogen-exchange reaction with NaI in acetone; see:
-
11b 2-Chloro-3-formylquinoline
was prepared by the Vilsmeier-Haack reaction of acetanilide
with POCl3 and DMF; see:
Meth-Cohn O.Narine B.Tarnowski B. J. Chem. Soc., Perkin Trans. 1 1981, 1520 -
11a
Meth-Cohn O.Narine B.Tarnowski B.Hayes R.Keyzad A.Rhouati S.Robinson A. J. Chem. Soc., Perkin Trans. 1 1981, 2509 -
12a
Tobia D.Rickborn B. J. Org. Chem. 1987, 52: 2611 -
12b
Payne AD.Wege D. Org. Biomol. Chem. 2003, 1: 2383 -
12c
Mukherjee S.Jana GP.Ghorai BK.
J. Organomet. Chem. 2009, 694: 4100 - 13
Sarkar TK.Panda N.Basak S. J. Org. Chem. 2003, 68: 6919 - 14
Li R.Zhang L.Camacho-Davila A.Herndon JW. Tetrahedron Lett. 2005, 46: 5117 -
15a For
a review on isobenzofurans, see:
Friedrichsen W. Adv. Heterocycl. Chem. 1999, 73: 1 -
15b
Rodrigo R. Tetrahedron 1988, 44: 2093 - 16
Camacho-Davila A.Herndon JW. J. Org. Chem. 2006, 71: 6682