Areno [E]indols, preparation method and application as intermedi

Details Areno [E]indols, preparation method and application as intermedi Areno [E]indols, preparation method and application as intermedi

1994-05-19

1996-11-05

Haley, Jacqueline

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548429, C07D48702, C07D20956

Patent

active

055719279

ABSTRACT:
The areno[e]indols have the formula (I). The methods comprises: (a) reacting (VI) with an aldehyde Ar"--CHO to obtain (VII); (b) oxidizing (VII) to yield the cetone (VIII); (c) reating (VIII) with a strong base and thereafter with an acycle chloride ClCOR, to produce (IX); (d) subjecting to a photochemical cyclization (IX) to produce (I). In said formulas Ar is phenyl or substituted phenyl; Ar' is radical (i) or (ii); R is an acyle group, Ar" is a phenyl, pyrolyl, furanyl or thiophenyl group substituted up to three times by any of the radials R, R.sup.1, R.sup.2, or R.sup.3. The compounds (I) are useful as intermediates in the synthesis of hexahydroareno(e)cyclopropa(c)indol-4-ones with antitumoral activity.

REFERENCES:
"Studies on the Synthesis of the Antitumor Agent CC-1065 Synthesis of PDE I and PDE II, Inhibitors of Cyclic Andenosine-3',5'-Monophosphate Phosphodiesterase Using the 3, 3'-Bipyrrole Strategy"-P. Magnus et al. (Journal of the American Chemical Society, vol. 109, No. 9, 1987) -See p. 2714, Formula 44, 45, & 49.
F. B. Mallory and C. W. Mallory, Organic Reactions, 30, (1984).
V. H. Rawal, R. J. Jones, M. P. Cava, Tetr.Letters; 26, p. 2423 (1985).
V. H. Rawal, R. J. Jones. M. P. Cava, J. Org. Chem., 52, p. 19 (1987).
K. Drost, M. P. Cava, J. Org. Chem., 56, p. 2240 (1991).
V. H. Rawl, R. J. Jones, M. P. Cava, Heterocycles, 25 p. 701 (1987) (Document IV).

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