Benzisothiazole and naphtho-1,2-thiazine compounds

Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system

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544 33, 544 587, 544 69, 544229, 544368, 546 14, 546 94, 546198, 548110, 548207, 2602455, C07D41712, C07D27506

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active

043118399

ABSTRACT:
In one aspect, this invention relates to a method of synthesizing certain 3-(4'-OP-carbocyclic aryl)-3-(carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxides (and -2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides) by reacting (a) a 3-(4'-OP-carbocyclic aryl)-benz[d]isothiazole-1,1-dioxide wherein P is a protecting group or a 3-(4'-OP-carbocyclic aryl)-naphtho[1,8-de]-1,2-thiazine-1,1-dioxide wherein P is a protecting group and (b) a carbocyclic aryllithium compound to give (c) the corresponding 3-(4'-OP-carbocyclic aryl)-3-(carbocyclic aryl)-2,3-dihydrobenz[d]-isothiazole-1,1-dioxide or the corresponding 3-(4'-OP-carbocyclic aryl)-3-(carbocyclic aryl)-2,3-dihydronaphtho-[1,8-de]-1,2-thiazine-1,1-dioxide. In another aspect, the present invention relates to the 3,3-disubstituted-2,3-dihydrobenz[d]isothiazole-1,1-dioxides and the 3,3-disubstituted-2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides produced by the above-described method provided the 3,3 substituents are different, which compounds are useful in the synthesis of phenol and 1-naphthol sulfam(na)phthaleins employed, for example, as photographic optical filter agents and filter agent precursors.

REFERENCES:
Mustafa et al., J. Chem. Soc., (1952) pp. 1339-1340.
Abramovitch et al., J. Chem. Soc., Perkins Trans. I, 22, (1974), pp. 2589-2594.
Dutt, J. Chem. Soc., 121, pp. 2389-2394 (1922).
Houben-Weyl, Met. der Org. Chemie, vol. 13, (1970) pp. 189-190.
Beilstein's, Handbuch der Organ. Chemie, vol. 27, p. 534.

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