Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1980-12-22
1982-01-19
Jiles, Henry R.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
544 33, 544 587, 544 69, 544229, 544368, 546 14, 546 94, 546198, 548110, 548207, 2602455, C07D41712, C07D27506
Patent
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.
Borror Alan L.
Cincotta Louis
Foley James W.
Kampe Marcis M.
Campbell Sybil A.
Jiles Henry R.
Polaroid Corporation
Ramsuer R. W.
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