Partially Saturated Indeno[1,2-b]indole Derivatives via Deoxygenation of Heterocyclic α-Hydroxy-N,O-hemiaminals

Abstract

A series of 3-aminocyclohex-2-enones were reacted with indane-1,2,3-trione monohydrate (ninhydrin) yielding 4b,9b-dihydroxyindeno[1,2-b]indoles that were deoxygenated to indeno[1,2-b]indoles.

Key words

ninhydrin - deoxygenation - 3-aminocyclohex-2-enones - indeno[1,2-b]indoles - N,O-hemiaminals

References

• 2 Hemmerling H.-J. Janoschka M. Wunderlich H. Z. Naturforsch.  1993,  48b:  1094 
• 3 Dorlars A. In Houben-Weyl   4th ed., Vol. 11/2:  Georg Thieme Verlag; Stuttgart: 1958.  p.737 
• 4 Hemmerling H.-J. Merschenz-Quack A. Wunderlich H. Z. Naturforsch.  2004,  59b:  1143 
• 5 Chatterjie N. Shapiro R. Quo S.-G. Stephani RA. Tetrahedron Lett.  1975,  16:  2535 
• 6a Greenhill JV. Chem. Soc. Rev.  1977,  277 
• 6b Kuckländer U. In The Chemistry of Enamines   Rappoport Z. John Wiley & Sons; Chichester: 1994.  p.523 
• 6c Lue P. Greenhill JV. Adv. Heterocycl. Chem.  1997,  67:  207 
• 7a McCaldin DJ. Chem. Rev.  1960,  60:  39 
• 7b Schönberg A. Singer E. Tetrahedron  1978,  34:  1285 
• 8a Brown DW. Graupner PR. Sainsbury M. Shertzer HG. Tetrahedron  1991,  47:  4383 
• 9a Butera JA. Antane SA. Hirth B. Lennox JR. Sheldon JH. Norton NW. Warga D. Argentieri TM. Bioorg. Med. Chem. Lett.  2001,  11:  2093 
• 9b Antane SA, Butera JA, and Lennox JR. inventors; US  2001047026. 
• 10a Bal Ch. Baldeyrou B. Moz F. Lansiaux A. Colson P. Kraus-Berthier L. Léonce S. Pierre A. Boussard M. Rousseau A. Wierzbicki M. Bailly Ch. Biochem. Pharmacol.  2004,  68:  1911 
• 10b Wierzbicki M, Boussard M.-F, Rousseau A, Boutin A, and Delagrange P. inventors; EP  1245565. 
• 11 Miller CP, Collini MD, and Tran BD. inventors; US  6107292. 
• 12a

  Hemmerling H.-J., Götz C., Jose J.; Annual Meeting of the German Pharmaceutical Society (DPhG), Marburg 2006, Poster P32.

• 12b Hemmerling H.-J, Götz C, and Jose J. inventors; EP  2007/008624.  ; WO 2008040547, 2008
• 13 Robinson B. The Fischer Indole Synthesis   John Wiley & Sons; Chichester: 1982. 
• 14a Graham J. Ninan A. Reza K. Sainsbury M. Shertzer HG. Tetrahedron  1992,  48:  167 
• 14b Brown DW. Mahon MF. Ninan A. Sainsbury M. Shertzer HG. Tetrahedron  1993,  49:  8919 
• 14c Wang J.-B. Ji Q.-G. Xu J. Wu X.-H. Xie Y.-Y. Synth. Commun.  2005,  35:  581 
• 15a Estevez JC. Estevez RJ. Castedo L. Tetrahedron Lett.  1993,  34:  6479 
• 15b Reboredo FJ. Treus M. Estévez JC. Castedo L. Estévez RJ. Synlett  2002,  999 
• 16a Shapiro R. Chatterjie NJ. J. Org. Chem.  1970,  35:  447 
• 16b Bullington JL. Dodd JH. J. Org. Chem.  1993,  58:  4833 
• 16c Black DStC. Bowyer MC. Condie GC. Craig DC. Kumar N. Tetrahedron  1994,  50:  10983 
• 17a Edafiogho IO. Hinko CN. Chang H. Moore JA. Mulzac D. Nicholson JM. Scott KR. J. Med. Chem.  1992,  35:  2798 
• 17b Scott KR. Edafiogho IO. Richardson EL. Farrar VA. Moore JA. Tietz EI. Hinko CN. El-Assadi A. Nicholson JM. J. Med. Chem.  1993,  36:  1947 
• 17c Greenhill JV. Chaaban I. Steel PJ. J. Heterocycl. Chem.  1992,  29:  1375 
• 17d Kesten SJ. Degnan MJ. Hung J. McNamara DJ. Ortwine DF. Uhlendorf SE. Werbel LM. J. Med. Chem.  1992,  35:  3429 
• 18a King JA. McMillan FH. J. Am. Chem. Soc.  1950,  72:  1238 
• 18b Ziegler FE. Bennett GB. J. Am. Chem. Soc.  1973,  95:  7458 

1

Present address: Dr. Hans-J. Hemmerling, Großes Feld 21, 40822 Mettmann, Germany.

19

Scattering factors, dispersion corrections and absorption coefficients were taken from International Tables for Crystallography (1992, Vol. C). Crystallographic data for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC 694526 (9B1) and CCDC 694527 (10B5). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: [phone]; or
e-mail: [e-mail]].

20

SHELXS-86: Sheldrick, G. M., Universität Göttingen, 1985.

21

SHELXL-97: Sheldrick, G. M., Universität Göttingen, 1997.