Novel synthesis of 3,3-substituted dihydrobenzisothiazole-1,1-di

Details Novel synthesis of 3,3-substituted dihydrobenzisothiazole-1,1-di Novel synthesis of 3,3-substituted dihydrobenzisothiazole-1,1-di

1977-09-23

1979-12-11

Daus, Donald G.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

260239R, 2602455, 544 62, 544135, 544368, 546 95, 546198, 548209, C07D27506

Patent

active

041784472

ABSTRACT:
This invention relates to a method of synthesizing certain 3-(carbocyclic aryl)-3-(4'-OP-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 4-OP-carbocyclic aryllithium compound wherein P is a protecting group and (b) a 3-(carbocyclic aryl)benz[d]isothiazole-1,1-dioxide wherein said 3-(carbocyclic aryl) moiety is other than a 3-(4'-OP-carbocyclic aryl) moiety to give (c) the corresponding 3-carbocyclic aryl)-3-(4'-OP-carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxide. The -2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides are prepared in the same manner by reacting a 3-(carbocyclic aryl)naphtho[1,8-de]-1,2-thiazine-1,1-dioxide with said 4'-OP-carbocyclic aryllithium compound.
In a further embodiment, the compounds synthesized according to the foregoing method are reacted with a carboxylic acid halide to give the corresponding 2-carbonyl-substituted 2,3-dihydrobenz[d]isothiazole-1,1-dioxide (or -2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides) followed by removing the protecting group, P, with weak acid to yield certain phenol and 1-naphthol sulfam(na)phthaleins useful, e.g., as optical filter agents and filter agent precursors in photography.

REFERENCES:
Beilstein, "Hand Buch der Organischen Chemie", vol. 27, p. 534.
Houben-Weil, "Met. der Org. Chemie", vol. 13, (1970), pp. 189-190.
McClelland et al., "J. Chem. Soc.", (1940), pp. 323-327.
Abramovitch, R. A., et al., "J. Chem. Soc.", Perkin Translation I, 22, pp. 2589-2594 (1974).
"Protective Groups in Organic Chemistry," Editor J. F. W. McOmie, Plenum Press, N.Y., 1973 (Chap. IV, Haslam), pp. 145-147.
Dutt, S., J. Chem. Soc., 121, pp. 2389-2394 (1922).

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