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

C - Chemistry, Metallurgy

07

D

260/273, 260/317

C07D 213/75 (2006.01) C07D 209/30 (2006.01) C07D 209/86 (2006.01) C07D 209/88 (2006.01) C07D 471/04 (2006.01)

Patent

CA 1043337

ABSTRACT OF THE DISCLOSURE 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 azo- sulfonium 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 users, e.g., in making perfumes, dyes, amino acids, pharma- ceuticals, agricultural chemicals and the like. -1-

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