Synthesis of indoles from anilines and intermediates therein

Details Synthesis of indoles from anilines and intermediates therein Synthesis of indoles from anilines and intermediates therein

1975-04-30

1976-11-16

Rotman, Alan L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602948G, 26032611R, 26032612R, 26032613R, 260315, 260551S, C07D21336

Patent

active

039923924

ABSTRACT:
Preparing indoles and intermediates therefor by reacting an N-haloaniline with a .beta.-carbonylic hydrocarbon sulfide to form an azasulfonium halide, reacting the azasulfonium halide with a strong base to form a thio-ether indole derivative, and then reducing the thio-ether indole, e.g. with Raney nickel, to form the indole compound. When an acetal or ketal of the .beta.-carbonyl hydrocarbon sulfide is used, the azasulfonium salt is treated with a base, and then with an acid to form the thio-ether indole derivative. When an .alpha.-ethyl-.beta. -carbonylic hydrocarbon sulfide is used, the resulting azosulfonium salt reacts with strong base to form a thio-ether indolenine derivative, which on reduction with Raney nickel or complex metal hydrides yields 3-substituted indoles. The aniline may be an aminopyridine to form an aza-indole compound in the process. The azasulfonium salts and thio-ether indole or thio-ether indolenine derivatives can be isolated and recovered from their respective reaction mixtures. The thio-ether-indole and thio-ether indolenine derivatives are useful as intermediates to make the indoles without the thio-ether group. The indoles are known compounds having a wide variety of uses, e.g., in making perfumes, dyes, amino acids, pharmaceuticals, agricultural chemicals and the like.

REFERENCES:
gassman et al., J. Am. Chem. Soc., vol. 95 p. 590 Jan. 24, 1972.
Gassman et al., J. Am. Chem. Soc. vol. 95 (2) pp. 591-592 Jan. 24, 1972.
Gassman et al., Journal Amer. Chem. Soc., vol. 96, pp. 5495-5508 (1974).

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