Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1976-08-09
1978-03-21
Jiles, Henry R.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
26032627, 2603265S, 26032662, 2603269, C07D20988
Patent
active
040803414
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, "Chem. Abstracts" vol. 83, (1975), No. 193,079c.
Gassman et al., "J. Amer. Chem. Soc." vol. 95, (1972), pp. 590-592.
Gassman et al., "J. Amer. Chem. Soc." vol. 96, (1974), pp. 5495-5508.
Hueschen Gordon W.
Jiles Henry R.
Ramsuer R. W.
The Ohio State University Research Foundation
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