Certain N-phenyl or N-pyridyl aza sulfonium salts

Details Certain N-phenyl or N-pyridyl aza sulfonium salts Certain N-phenyl or N-pyridyl aza sulfonium salts

1976-08-09

1978-01-10

Rotman, Alan L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

560138, 560142, 560 18, 2602948G, 2602948F, 2602948D, 2603407, 2603409R, 260465E, 260551S, C07D21362

Patent

active

040678750

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., 95, 588 (1973).
Gassman et al., J. Am. Chem. Soc., 95, 590 (1973).
Gassman et al., J. Am. Chem. Soc., 94, 3884 (1972).
Wick et al., J. Agr. Food Chem., 9, 289 (1961).

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