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Synthesis 2009(18): 3051-3060
DOI: 10.1055/s-0029-1216919
DOI: 10.1055/s-0029-1216919
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Studies on the Chemistry of 2-[3-(2-Nitrophenyl)-2-oxopropyl]benzaldehydes: Novel Syntheses of 5H-Benzo[b]carbazole-6,11-diones and Indolo[1,2-b]isoquinoline-6,11-diones
Further Information
Received
10 February 2009
Publication Date:
23 July 2009 (online)
Publication History
Publication Date:
23 July 2009 (online)
Abstract
Syntheses of 5H-benzo[b]carbazole-6,11-diones and indolo[1,2-b]isoquinoline-6,11-diones are described. Both compounds are synthesized from 2-[3-(2-nitrophenyl)-2-oxopropyl]benzaldehydes, which were obtained from commercially available indan-1-ones in six steps.
Key words
ozonolysis - ketoaldehyde - aldol condensation - hydrogenation - indole
- 1
Taylor DA.Mehdi Baradarani M.Martínez SJ.Joule JA. J. Chem. Res., Synop. 1979, 387 ; J. Chem. Res., Miniprint 1979, 4801 - 2
Biochemistry
of Quinones
Morton RA. Academic Press; New York: 1965. - 3
Bernardo PH.Chai CLL.Le Guen M.Smith GD.Waring P. Bioorg. Med. Chem. Lett. 2007, 17: 82 -
4a
Cheng CC. Progress in Medicinal Chemistry Vol. 25:Ellis GP.West GB. Elsevier; Amsterdam: 1988. -
4b
Asche C.Frank W.Albert A.Kucklaender U. Bioorg. Med. Chem. 2005, 13: 819 -
5a Luo
Y.-L., Chou T.-C., Cheng C. C.; J. Heterocycl. Chem.; 1996, 33: 113
-
5b Mocellin S.; Microarray Technology and Cancer Gene Profiling;
Springer: Heidelberg, 2007; Chap. 8, 98
-
6a
Bennasar M.-Ll.Roca T.Ferrando F. J. Org. Chem. 2005, 70: 9077 -
6b
Bernardo PH.Chai CLL.Heath GA.Mahon PJ.Smith GD.Waring P.Wilkes BA. J. Med. Chem. 2004, 47: 4958 -
6c
Mal D.Senapati BK.Pahari P. Tetrahedron 2007, 63: 3768 -
6d
Ashcroft WR.Dalton L.Beal MG.Humphrey GL.Joule JA. J. Chem. Soc., Perkin Trans. 1 1983, 2409 -
7a
Hagelin H.Oslob JD.Akermark B. Chem. Eur. J. 1999, 5: 2413 -
7b
Knoelker H.-J.O’Sullivan N. Tetrahedron 1994, 50: 10893 -
7c
O’Sullivan PJ.Moreno R.Murphy WS. Tetrahedron Lett. 1992, 33: 535 -
7d
Bittner S.Krief P.Massil T. Synthesis 1991, 215 - 8
Fernández M.Barcia C.Estévez JC.Estévez RJ.Castedo L. Synlett 2004, 267 -
9a
Cruces J.Martínez E.Treus M.Martínez LA.Estévez JC.Estévez RJ.Castedo L. Tetrahedron 2002, 58: 3015 -
9b
Estévez JC.Estévez RJ.Castedo L. Tetrahedron Lett. 1993, 34: 6479 - 10
Cruces J.Estévez JC.Castedo L.Estévez RJ. Tetrahedron Lett. 2001, 42: 4825 - 11
Barcia JC.Cruces J.Estévez JC.Estévez RJ.Castedo L. Tetrahedron Lett. 2002, 43: 5141 -
12a
Gribble GW.Saulnier MG.Obaza-Nutaitis JA.Ketcha DM. J. Org. Chem. 1992, 57: 5891 -
12b
Merour JY.Piroelle S.Cossais F. Heterocycles 1993, 36: 1287 -
12c
Fraser HL.Gribble GW. Can. J. Chem. 2001, 79: 1515 -
14a
Hooper M.Pitkethly WN. J. Chem. Soc., Perkin Trans. 1 1972, 1607 -
14b
Rajeswaran WG.Srinivasan PC. Synthesis 1994, 270 -
14c
Bennasar M.-L.Roca T.Ferrando F. Tetrahedron Lett. 2004, 45: 5605 - 15
Nieman JA.Keay BA. Tetrahedron: Asymmetry 1995, 6: 1575 - 16
Campbell N.Davison PS.Heller HG. J. Chem. Soc. 1963, 993 - 17
Kometani T.Yoshii E. J. Chem. Soc., Perkin Trans. 1 1981, 1191 - 18
Ko K.-Y.Eliel EL. J. Org. Chem. 1986, 51: 5353 - 19
Martínez A.Fernández M.Estévez JC.Estévez RJ.Castedo L. Tetrahedron 2005, 61: 1353 - 20
Wolinsky J.Slabaugh MR.Gibson T. J. Org. Chem. 1964, 29: 3740 - 21
Barton DHR.Brewster AG.Ley SV.Read CM.Rosenfeld MN. J. Chem. Soc., Perkin Trans. 1 1981, 1473 - 22
Mackenzie NE.Surendrakumar S.Thomson RH.Cowe HJ.Cox PJ. J. Chem. Soc., Perkin Trans. 1 1986, 2233 - 23
Martínez A.Fernández M.Estévez JC.Estévez RJ.Castedo L. Tetrahedron 2005, 61: 485 - 24
Cruces J.Estévez JC.Estévez RJ.Castedo L. Heterocycles 2000, 53: 1041 - 25
Robineon RK.Moeettig E. J. Am. Chem. Soc. 1939, 61: 1148 - 26
Perrin DD.Armarego WLF. Purification of Laboratory Chemicals Pergamon; Oxford: 1988.
References
http://www.ncbi.nlm.nih.gov/sites/entrez, search PubChem Compound for CID362142.