Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1980-08-04
1982-11-16
Rizzo, Nicholas S.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
544 587, 544 62, 544368, 260239R, 546209, 548208, 548209, C07D27504, C07D27908
Patent
active
043595740
ABSTRACT:
In one aspect, this invention relates to a method of synthesizing certain 3-(4'-OH-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 3-(4'-OP-carbocyclic aryl)-3-(carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxide (or a 3-(4'-OP-carbocyclic aryl)-3-(carbocyclic aryl)-2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxide) wherein P is a protecting group with a carboxylic acid halide in pyridine to yield the corresponding 2-carbonyl derivative followed by removing the protecting group with weak acid to give the product. Optionally, the acylation step may be carried out by sequentially reacting the starting compound with an alkali metal hydride to give the corresponding 2-alkali metal salt and then reacting with the carboxylic acid halide in a suitable inert organic solvent. The products produced comprise phenol and 1-naphthol sulfam(na)phthaleins useful, for example, as photographic optical filter agents and filter agent precursors.
In another aspect, the present invention relates to the carbonyl-substituted and alkali metal-substituted 2,3-dihydrobenz[d]isothiazole-1,1-dioxides and 2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides produced as intermediates in the above synthesis.
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Bloom Stanley M.
Borror Alan L.
Foley James W.
Campbell Sybil A.
Polaroid Corporation
Rizzo Nicholas S.
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