Process for the direct and regioselective functionalization in p

Details Process for the direct and regioselective functionalization in p Process for the direct and regioselective functionalization in p

1992-03-02

1993-03-02

Berch, Mark

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D27920, C07B 4504

Patent

active

051910780

ABSTRACT:
A process for the direct and regioselective functionalization of phenothiazine which allows one to introduce an SH group in position 2 is described. The thus-obtained 2-mercapto-phenothiazine is easily transformed into 2-methylthio-phenothiazine, an important intermediate for the preparation of pharmacological active compounds. One of the reaction routes (described in detail in the specification) involves the production of an N-aryl-phenothiazine-2-sulfinic acid [compound (III)] which can be isolated as a salt (e.g., an alkaline salt) by treatment with an aqueous alkaline solution. Thus compound (III-A) is produced.

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patent: 5089613 (1992-02-01), Meneghin
Heterocycles, vol. 26, No. 1, 1987, Saraf et al., "Recent Advances in the Synthesis of Phenothiaines", pp. 239-273.
Knoevenagel Berichte, 1909, pp. 3315-3322.
Chemical Abstracts, vol. 77, No. 19661c (1972), Wanzlick, "3-Mercapto- and 3-(alkylthio)phenothiazines" and DE 2,047,078.
Encyclopedia of Chemical Technology 3rd edition, Kirk-Othmer, vol. 11, (1980), p. 287.
"Reductions in Organic Chemistry," 1986, Hudlicky, p. 90.

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