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Reactions of Aza-ortho-xylylenes Generated from 3-Aryl-2,1-benzisothiazoline 2,2-Dioxides

Modrzejewska H., Wojciechowski K.

Polish Journal of Chemistry

2006

Vol. 80, nr 10

1695-1702

3-Methyl-3-(4-nitrophenyl)-2,1-benzisothiazoline 2,2-dioxides 1a,b undergo thermal extrusion (180°C) of SO2 to form aza-ortho-xylylenes, which after [1,5]-hydrogen shift give 1,1-diarylethylenes 9a,b. The corresponding 3-(nitropyridinyl) benzosultams undergo transformation into dihydro-azepino[2,3-b]indole derivatives 17.

Reactions of 1-Arylbuta-1,3-dienes Generated from 3-Allyl-1,3-dihydro-2,1-benzisothiazole 2,2-Dioxides

Wojciechowski K., Modrzejewska H.

Polish Journal of Chemistry

2002

Vol. 76 / nr 11

1587-1593

Thermal (215_C) extrusion of sulfur dioxide from 3-allyl-1,3-dihydro-2,1-benzisothiazole 2,2-dioxides (3-allylbenzosultams) leads to aza-ortho-xylylenes, which by [1,5] sigmatropic hydrogen shift transform into 1-(2-aminophenyl)buta-1,3-dienes. In the presence of dienophiles, N-phenylmaleimide (NPMI) or dimethyl fumarate, these dienes enter Diels-Alder reaction and the formed adducts transform into 6a,7,8,10a-tetrahydro-5H-phenanthridin-6-one derivatives. Aza-ortho-xylylene 16 generated from 3,3-diallylbenzosultam 15 transforms into arylcyclohexadiene 19, which finally adds NPMI to form bicyclo[2.2.2]octene derivative 20.

Reactions of aza-ortho-xylylenes with 1,4-naphthoquinone

Kosiński Sz., Wojciechowski K.

Polish Journal of Chemistry

1998

Vol. 72, nr 12

2546-2550

Reactions of 1,4-naphthoquinone with aza-ortho-xylylenes generated via thermal extrusion of SO2 from 2,1-benzisothiazoline 2,2-dioxides (benzosultams) lead to tetrahydronaphthalene-2-spiro-2'-dihydroindole derivatives. Aza-ortho-xylylene generated via thermal ring opening of 1-phenylbenzazetidine gave with naphthoquinone benzo[b]acridine deritative 15.